Diisopropylethylamine → 1-[[2-(3-chlorophenyl)-5-cyclopropyl-2H-pyrazol-3-yl]-methyl]-3-[3-fluoro-4-(2-methylsulfonyl-ethyl)-phenyl]-urea

HRID 1843032Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][S:10]([CH3:13])(=[O:12])=[O:11].[Cl:24][C:25]1[CH:26]=[C:27]([N:31]2[C:35]([CH2:36][NH2:37])=[CH:34][C:33]([CH:38]3[CH2:40][CH2:39]3)=[N:32]2)[CH:28]=[CH:29][CH:30]=1.C(N(C(C)C)C(C)C)C>C1COCC1>[Cl:24][C:25]1[CH:26]=[C:27]([N:31]2[C:35]([CH2:36][NH:37][C:15]([NH:14][C:4]3[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][S:10]([CH3:13])(=[O:11])=[O:12])=[C:2]([F:1])[CH:3]=3)=[O:23])=[CH:34][C:33]([CH:38]3[CH2:39][CH2:40]3)=[N:32]2)[CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of phenyl 3-fluoro-4-(2-(methylsulfonyl)ethyl)phenylcarbamate (90 mg, 0.267 mmol) and (1-(3-chlorophenyl)-3-cyclopropyl-1H-pyrazol-5-yl)methanamine (70 mg, 0.286 mmol) in THF (4 mL) was added N-ethyldiisopropylamine (0.087 mL, 0.507 mmol) and stirred for 1 h in a microwave (150° C., 7 bar). The reaction mixture was concentrated in vacuo and purified by CC (eluent: ethyl acetate/cyclohexane (2:1)) to give 1-[[2-(3-chlorophenyl)-5-cyclopropyl-2H-pyrazol-3-yl]-methyl]-3-[3-fluoro-4-(2-methylsulfonyl-ethyl)-phenyl]-urea (30 mg, 23%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
custompurified by CC (eluent: ethyl acetate/cyclohexane (2:1))

Sources & evidence

ORD record: ord-1c9d7850c8844381ab87264d89d7a05c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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