Reaction #674324

ord-767ef83c1368434baf155ca5a5f03ae8

Reaction equation

COCC1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
B4
COCC1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
rac-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
intermediates A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
A2
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenesulfonamide
→
COC[C@H]1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
B5
COC[C@H]1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
(R)-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

Reactants

COCC1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
B4
COCC1CCCCN1c1ncnc(Nc2cccc(CS(N)(=O)=O)c2)n1
rac-3-[(4-(2-Methoxymethylpiperidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
intermediates A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
A2
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenesulfonamide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherobtained as a white crystalline solid

Procedure

B5 was prepared following the procedure reported for B4 using the intermediates A1 and A2 and obtained as a white crystalline solid; yield: 90 mg (25%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 1.27-1.90 (m, 4H), 2.48-2.60 (m, 2H), 2.90-3.03 (m, 1H), 3.38 (s, 3H), 3.61 (bs, 2H), 4.26 (s, 2H), 4.61-4.75 (m, 1H), 5.03-5.15 (m, 1H), 6.90 (bs, 2H), 7.03-7.10 (m, 1H), 7.28-7.40 (m, 1H), 7.62-7.73 (m, 1H), 7.82 (bs, 1H), 8.28 (s, 1H), 9.68 (bs, 1H). MS (ES) C17H24N6O3S requires: 392. found: 393 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09226929B2uspto-grants-2016_01