4-(Chlorosulfonyl)benzoic acid → HCID 58614909, compound

HRID 923034Notes

Reaction equation

ClS(C1C=CC(C(O)=O)=CC=1)(=O)=O.N1(C(=O)C)CCNCC1.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][C:25]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1.[C:37]([N:40]1[CH2:45][CH2:44][N:43]([S:46]([C:49]2[CH:57]=[CH:56][C:52]([C:53](O)=[O:54])=[CH:51][CH:50]=2)(=[O:48])=[O:47])[CH2:42][CH2:41]1)(=[O:39])[CH3:38]>>[C:37]([N:40]1[CH2:45][CH2:44][N:43]([S:46]([C:49]2[CH:57]=[CH:56][C:52]([C:53]([NH:28][C:27]3[CH:29]=[CH:30][C:24]([Cl:23])=[C:25]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)[CH:26]=3)=[O:54])=[CH:51][CH:50]=2)(=[O:47])=[O:48])[CH2:42][CH2:41]1)(=[O:39])[CH3:38]

Participants

Reactant 4

HCID 823854-(Chlorosulfonyl)benzoic acid

HCID 837951-Acetylpiperazine

HCID 7730578HCID 7730578, compound

HCID 401519254-Chloro-3-(pyridin-2-yl)aniline

Product 1

HCID 58614909HCID 58614909, compound

Procedure

1 g of 4-(chlorosulfonyl)benzoic acid was reacted with 646 μL of 1-(piperazin-1-yl)ethanone via Procedure H. 75 mg of 4-chloro-3-(pyridin-2-yl)aniline was coupled to 125 mg of 4-(4-acetylpiperazin-1-ylsulfonyl)benzoic acid via Procedure G and purified by reverse phase HPLC to yield 4-(4-acetylpiperazin-1-ylsulfonyl)-N-(4-chloro-3-(pyridin-2-yl)phenyl)benzamide. MS (Q1) 499.4 (M)+.

Workup

custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-bacaa4bedc094d0080f1f662f7a48525
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278961B2

Reaction notes

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