Reaction #674343

ord-3ed22f00b73a4e39831cde877448d539

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
Nc1cccc(CCS(N)(=O)=O)c1
A3
Nc1cccc(CCS(N)(=O)=O)c1
2-(3-Aminophenyl)ethanesulfonamide
→
NS(=O)(=O)Cc1cccc(Nc2ncnc(N3CCC[C@@H]3COc3ccccc3)n2)c1
(R)-3-[(4-(2-(Phenoxymethyl)pyrrolidin-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
Nc1cccc(CCS(N)(=O)=O)c1
A3
Nc1cccc(CCS(N)(=O)=O)c1
2-(3-Aminophenyl)ethanesulfonamide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherB28 was prepared
  2. 2
    OtherIt was obtained as a white crystalline powder

Procedure

B28 was prepared following the procedure reported for B4 using the intermediates A1 and A3. It was obtained as a white crystalline powder; yield: 140 mg (35%). MS (ES) C21H24N6O3S requires: 440. found: 441 (M+H)+.

Source

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