Morpholine → HCID 59631812, compound

HRID 2369044Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:14]=[C:15]([C:29](O)=[O:30])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=3)=[CH:17][CH:18]=2)=[CH:11][C:10]([C:32]([F:35])([F:34])[F:33])=[N:9]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:28])(=[O:26])=[O:27])[CH:20]=3)=[C:15]([C:29]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[O:30])[CH:14]=2)=[CH:11][C:10]([C:32]([F:34])([F:35])[F:33])=[N:9]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 4-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3′-(methylsulfonyl)biphenyl-2-carboxylic acid (0.52 g, 1 mmol) in DCM (6 mL) was added carbonyldimidazole (2.43 mg, 1.5 mmol) and the mixture was stirred for 2 h at 20° C. Morpholine (0.175 mL, 2 mmol) was added and the mixture was stirred overnight at 20° C. Evaporation of solvent gave a crude, which was purified by column chromatography on silica gel eluting with EtOAc-hexane (1:4 to 4:1) to afford (4-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)-3′-(methylsulfonyl)biphenyl-2-yl)(morpholino)methanone (0.52 g). 1H-NMR (CDCl3): δ 7.97 (m, 2H), 7.77 (d, 1H), 7.64 (m, 1H), 7.58 (m, 1H), 7.46-7.24 (m, 5H), 6.89 (s, 1H), 3.55 (m, 3H), 3.33 (m, 2H), 3.08 (s, 3H), 2.87 (m, 2H), 2.69 (m, 1H). MS(ES): 590 [M+H]+.

Workup

stirringthe mixture was stirred overnight at 20° C
customEvaporation of solvent
customgave a crude, which
customwas purified by column chromatography on silica gel eluting with EtOAc-hexane (1:4 to 4:1)

Sources & evidence

ORD record: ord-eead0076cc25472d936bae513d243c0a
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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