Benzenesulfonamide → 2,5-dimethyl-N-[(1S)-1-(4-{[(phenylsulfonyl)amino]carbonyl}phenyl)ethyl]-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

HRID 870070Notes

Reaction equation

HRID 870070 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:32])=[C:5]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)[CH3:11])=[O:8].[C:33]1([S:39]([NH2:42])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1>[CH3:1][C:2]1[S:3][C:4]([CH3:32])=[C:5]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=2)[C:6]=1[C:7]([NH:9][C@H:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:42][S:39]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:41])=[O:40])=[O:18])=[CH:19][CH:20]=1)[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 249529274-{(1S)-1-[({2,5-dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid

Product 1

HCID 249532822,5-dimethyl-N-[(1S)-1-(4-{[(phenylsulfonyl)amino]carbonyl}phenyl)ethyl]-4-[4-(trifluoromethyl)benzyl]thiophene-3-carboxamide

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-{(1S)-1-[({2,5-Dimethyl-4-[4-(trifluoromethyl)benzyl]-3-thienyl}carbonyl)amino]ethyl}benzoic acid from Example 12 (200 mg, 0.433 mmol) was treated with benzenesulfonamide (85.0 mg, 0.542 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (166 mg, 0.866 mmol) and 4-dimethylaminopyridine (66.0 mg, 0.542 mmol) under conditions similar to Example 18. The crude was purified by Combi Flash chromatography system (25% THF/CHCl3 for 5 min., then 50% for 5 min.) to afford the desired product as a white solid. MS (−APCI): m/z 599 (M−1)−.

Workup

  1. customThe crude was purified by Combi Flash chromatography system (25% THF/CHCl3 for 5 min.

Sources & evidence

ORD record
ord-5fc69413dcca498f9172d0ad800a953f
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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