Diisopropylethylamine → N-Phenyl-4-[1-phenyl-5-[(phenylsulfonyl)amino]-1H-pyrazol-3-yl]benzamide

HRID 1860524Notes

Reaction equation

HRID 1860524 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2N=N1.[C:34]1([S:40]([NH:43][C:44]2[N:48]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:47]=[C:46]([C:55]3[CH:63]=[CH:62][C:58]([C:59]([OH:61])=O)=[CH:57][CH:56]=3)[CH:45]=2)(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CN(C1C=CN=CC=1)C.O>[C:12]1([NH:8][C:59](=[O:61])[C:58]2[CH:62]=[CH:63][C:55]([C:46]3[CH:45]=[C:44]([NH:43][S:40]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)(=[O:42])=[O:41])[N:48]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:47]=3)=[CH:56][CH:57]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:11]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27960291-Hydroxybenzotriazole hydrateHCID 698310104-(5-benzenesulfonylamino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid

Product 1

HCID 12018686N-Phenyl-4-[1-phenyl-5-[(phenylsulfonyl)amino]-1H-pyrazol-3-yl]benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzotriazol-1-yloxytripyrrolid inophosphonium hexafluorophosphate (0.136 g, 0.26 mmol) was added to a solution of 4-(5-benzenesulfonylamino-1-phenyl-1H-pyrazole-3-yl)-benzoic acid (0.10 g, 0.24 mmol) and N,N-diisopropylethylamine (0.062 ml, 0.36 mmol) in N,N-dimethylformamide (2 ml). 1-Hydroxybenzotriazole hydrate (30 mg, 0.24 mmol) and 4-(N,N-dimethylamino)pyridine (catalytic) were added and the resulting solution was stirred at room temperature for 3 hours. Water (7 ml) was added, and a precipitate was collected by filtration and washed with water. The solid was purified by preparative thin layer silica gel chromatography, using 2% methanol in dichloromethane as the eluant, to yield N-Phenyl-4-[1-phenyl-5-[(phenylsulfonyl)amino]-1H-pyrazol-3-yl]benzamide as a colorless solid.

Workup

  1. filtrationa precipitate was collected by filtration
  2. washwashed with water
  3. customThe solid was purified by preparative thin layer silica gel chromatography

Sources & evidence

ORD record
ord-03e0f0edbacd4ac6b245c68962c0e973
Source dataset
uspto-grants-2003_03
Patent number
US06531478B2

Reaction notes

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