Aniline → HCID 20800066, compound

HRID 1071737Notes

Reaction equation

HRID 1071737 reaction equation
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)=[O:12])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18](=[O:20])[NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)=[O:12])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 220644524-({[(5-Chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoic acid

Product 1

HCID 20800066HCID 20800066, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-({[(5-chloro-2-thienyl)sulfonyl]amino}carbonylamino)benzoic acid (69 mg) in DMF (0.7 mL) was added aniline (21 uL, 0.23 mmol), DIEA (3 eq.) then PyBOP (85 mg, 0.16 mmol). The reaction mixture was stirred at room temp for 28 hr, acidified and HPLC purified to give {[(5-chloro(2-thienyl))sulfonyl]amino}-N-[4-(N-phenylcarbamoyl)phenyl]carboxamide (29 mg, 45%). ES-MS (M+H)+=436, 438 (Cl).

Workup

  1. customHPLC purified

Sources & evidence

ORD record
ord-f22ff49705bc45219ac36fda93d0168f
Source dataset
uspto-grants-2005_06
Patent number
US06906063B2

Reaction notes

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