Diisopropylethylamine → butyl [3-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]carbamate

HRID 1694853Notes

Reaction equation

[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:29][C:30]1[C:34]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])(C)C)=[CH:33][N:32]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:31]=1.[CH:49](N(CC)C(C)C)(C)[CH3:50].F[P-](F)(F)(F)(F)F.N1(O[P+](C(C)C)(C(C)C)C(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[NH:12]([C:10](=[O:11])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:29][C:30]2[C:34]([NH:35][C:36](=[O:42])[O:37][CH2:38][CH2:41][CH2:49][CH3:50])=[CH:33][N:32]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[N:31]=2)=[O:25])=[CH:21][CH:20]=1)[C:8]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (0.3 g, 0.8 mmol), tert-butyl (3-amino-1-phenyl-1H-pyrazol-4-yl)carbamate (0.28 g, 1.0 mmol) and N,N-diisopropylethylamine (0.11 g, 0.88 mmol) in methylene chloride (5 mL) was added (1H-1,2,3-benzotriazol-1-yloxy)(triisopropyl)phosphonium hexafluorophosphate (0.53 g, 1.2 mmol). The reaction vessel was sealed and heated to 60° C. for 16 hours. The product was purified by flash chromatography (0-3% methanol/methylene chloride) to give crude ten-butyl [3-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)-1-phenyl-1H-pyrazol-4-yl]carbamate as a white solid. ESIMS calcd 631.3 (M++H), found 631.2 (M++H).

Workup

customThe reaction vessel was sealed
customThe product was purified by flash chromatography (0-3% methanol/methylene chloride)

Sources & evidence

ORD record: ord-96be8ccb743b4ea1a8f3ea94abd21b82
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158825B2

Reaction notes

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