Acetic Acid → (Z)-methyl 4-(2-oxo-2,3-dihydro-1H-thieno[2,3-e][1,4]diazepin-5-yl)benzoate

HRID 718123Notes

Reaction equation

[NH2:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=O)=[O:4].C(O)(=O)C>CO>[O:4]=[C:3]1[NH:5][C:6]2[S:7][CH:8]=[CH:9][C:10]=2[C:11]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[N:1][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

In a 75 mL pressure flask was suspended compound 492 (0.265 g, 0.832 mmol) and acetic acid (0.071 mL, 1.249 mmol) in methanol (20 mL) to give a yellow suspension. The reaction mixture was heated at 100° C. overnight. The solvent was removed to afford title compound 493 (250 mg, 100%) as a tan powder. MS (m/z): 301.3 (M+H).

Workup

customIn a 75 mL pressure flask was suspended
customThe solvent was removed

Sources & evidence

ORD record: ord-73cc5df108c44730911ffd29b8b1ed2a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Reaction notes

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