Hydrazine → HCID 178497404, compound

HRID 541323Notes

Reaction equation

[C:1]([C:4]1[C:5]([CH:15]2[CH2:18][CH2:17][CH2:16]2)=[CH:6][C:7]([CH3:14])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=O)[NH2:2].COC(OC)[N:22]([CH3:24])C.[NH2:27]N>C(O)(=O)C>[CH:15]1([C:5]2[C:4]([C:1]3[NH:22][CH:24]=[N:27][N:2]=3)=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH3:14])[CH:6]=2)[CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a vial was added methyl 5-carbamoyl-4-cyclobutyl-2-methylbenzoate (compound 202.1, 59 mg, 0.24 mmol, 1.0 equiv) and N,N-dimethylformamide dimethyl acetal (1 mL) was added. The mixture was heated at 80° C. for 5 hours then the solvents were removed in vacuo. To the residue was added acetic acid (400 μL) and a solution of anhydrous hydrazine (8.2 μL, 0.26 mmol, 1.1 equiv) in acetic acid (100.4). To the resulting thick suspension was added additional acetic acid (500 μL) and the mixture was stirred at 80° C. for 1.5 hours then the solvents removed in vacuo. Ethyl acetate (5 mL) and DCM (5 mL) was added (some undissolved solids). The organics was washed with saturated NaHCO3 (10 mL) and brine (5 mL) and removed in vacuo to obtain the title compound as a white solid (theoretical yield). m/z (ES+) 272 (M+H)+.

Workup

additionwas added
customthe solvents were removed in vacuo
additionTo the residue was added acetic acid (400 μL)
customthe solvents removed in vacuo
additionEthyl acetate (5 mL) and DCM (5 mL) was added (some undissolved solids)
washThe organics was washed with saturated NaHCO3 (10 mL) and brine (5 mL)
customremoved in vacuo

Sources & evidence

ORD record: ord-c2211f7a48ce4039905be41a8d062787
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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