Reaction #674351

ord-f8952f2ce02a448083b1d0123efc9a41

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
A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
c1ccc(C2CCN2)cc1
rac-2-phenylazetidine
→
NS(=O)(=O)Cc1cccc(Nc2ncnc(N3CCC3c3ccccc3)n2)c1
rac-3-[(4-(2-Phenylazetidin-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
A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
c1ccc(C2CCN2)cc1
rac-2-phenylazetidine

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherB37 was prepared
  2. 2
    Otherobtained as white crystals

Procedure

B37 was prepared following the general procedure reported for B4 using A1 and rac-2-phenylazetidine and obtained as white crystals; yield: 120 mg (34%). 1H NMR (300 MHz, d6-DMSO, 300K) δ 2.05-2.20 (m, 1H), 2.69-2.90 (m, 1H), 3.88-4.29 (m, 4H), 5.42 (bs, 1H), 6.72-7.08 (m, 3H), 7.20-7.55 (m, 6H), 7.58-7.72 and 7.82-8.00 (2 m, 1H), 8.11 and 8.25 (2bs, 1H), 9.65 and 9.78 (2bs, 1H). MS (ES) C19H20N6O2S requires: 396. found: 397 (M+H)+.

Source

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