Trifluoroacetic acid → N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(piperazin-1-ylsulfonyl)benzamide

HRID 633191Notes

Reaction equation

HRID 633191 reaction equation
ClS(C1C=CC(C(O)=O)=CC=1)(=O)=O.N1(C(OC(C)(C)C)=O)CCNCC1.[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][C:29]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1.C(OC([N:48]1[CH2:53][CH2:52][N:51]([S:54]([C:57]2[CH:65]=[CH:64][C:60]([C:61](O)=[O:62])=[CH:59][CH:58]=2)(=[O:56])=[O:55])[CH2:50][CH2:49]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>>[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:61](=[O:62])[C:60]2[CH:64]=[CH:65][C:57]([S:54]([N:51]3[CH2:52][CH2:53][NH:48][CH2:49][CH2:50]3)(=[O:56])=[O:55])=[CH:58][CH:59]=2)=[CH:30][C:29]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 823854-(Chlorosulfonyl)benzoic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 151696524-((4-((Tert-butoxy)carbonyl)piperazin-1-yl)sulfonyl)benzoic acidHCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614943N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(piperazin-1-ylsulfonyl)benzamide

Procedure

1 g of 4-(chlorosulfonyl)benzoic acid was reacted with 931 mg of tert-butyl piperazine-1-carboxylate via Procedure H. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 150 mg of 4-(4-(tert-butoxycarbonyl)piperazin-1-ylsulfonyl)benzoic acid via Procedure G. The crude product was subjected to basic workup conditions, treated with TFA to remove the Boc group and purified by reverse phase HPLC to yield N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(piperazin-1-ylsulfonyl)benzamide. MS (Q1) 457.1 (M)+.

Workup

  1. customto remove the Boc group
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-d3007ea14a5842b9b170f3d95e231458
Source dataset
uspto-grants-2016_04
Patent number
US09321761B2

Reaction notes

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