Acetic Acid → HCID 178452409, compound

HRID 473863Notes

Reaction equation

[C:1]1([CH2:7][NH:8][C:9](=S)[CH2:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]3[O:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][C:17]=3[CH:30]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:33][NH2:34].C(O)(=O)C.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=S)=CC=1>C(O)C>[C:1]1([CH2:7][NH:8][C:9]2[NH:34][N:33]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]4[O:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][C:17]=4[CH:30]=3)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 78 °C

Procedure

A mixture of 1,1-dimethylethyl 7-{3-[(phenylmethyl)amino]-3-thioxopropanoyl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (155 mg, 0.35 mmol), hydrazine monohydrate (66 mg, 0.59 mmol), acetic acid and Lawesson's reagent (63 mg, 1.0 mmol) in ethanol (5 mL) was stirred at 78° C. for one hour. The reaction mixture was cooled, concentrated and the residue purified directly by silica gel chromatography (5% methanol in dichlomethane) to give 1,1-dimethylethyl 7-{5-[(phenylmethyl)amino]-1H-pyrazol-3-yl}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (92 mg, 62% yield). MS (EI) for C24H28N4O3: 421 (MH+).

Workup

temperatureThe reaction mixture was cooled
concentrationconcentrated
customthe residue purified directly by silica gel chromatography (5% methanol in dichlomethane)

Sources & evidence

ORD record: ord-885436f69e294f158fd3b18fd98ad9a0
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637499B2

Reaction notes

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