Acetyl chloride → HCID 59632438, compound

HRID 2369086Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[Cl:25])[N:17]=[C:16]([C:26]([OH:29])([CH3:28])[CH3:27])[CH:15]=3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C(#N)C>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[N:18]1[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:37](=[O:39])[CH3:38])[CH:3]=3)=[CH:9][CH:10]=2)=[CH:15][C:16]([C:26]([OH:29])([CH3:27])[CH3:28])=[N:17]1

Participants

Conditions

Temperature: 75 °C

Procedure

To a solution of 2-(5-(3′-aminobiphenyl-4-yl)-1-(2-chlorophenyl)-1H-pyrazol-3-yl)propan-2-ol (370 mg, 037 mmol) in acetonitrile (1.6 mL) was added triethylamine (0.12 mL, 0.86 mmol) followed by acetyl chloride (27 μL, 380 μmol). The reaction vial was then shaken at 75° C. overnight. After cooling the reaction solution was concentrated under reduced pressure and the crude product was purified by flash column chromatography eluting with a gradient from 0% to 100% EtOAc/hexane to afford N-(4′-(1-(2-chlorophenyl)-3-(2-hydroxypropan-2-yl)-1H-pyrazol-5-yl)biphenyl-3-yl)acetamide (82 mg, 49% yield) as an oil. 1H NMR (400 MHz CDCl3): δ 7.79 (1H, s), 7.49-7.42 (4H, m), 7.41-732 (4H, m), 7.31-7.21 (3H, m), 6.54 (1H, s), 2.68 (1H, s), 2.19 (3H, s), 1.69 (6H, s). MS(ES): 445[M+H]+. The following compounds are prepared essentially according to the previous examples:

Workup

temperatureAfter cooling the reaction solution
concentrationwas concentrated under reduced pressure
customthe crude product was purified by flash column chromatography
washeluting with a gradient from 0% to 100% EtOAc/hexane

Sources & evidence

ORD record: ord-55deb90901bb4a19b3381e9fdc6b5e62
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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