Sodium Hydroxide → 6-Oxo-7,8,9,10-tetrahydro-6H-pyrido[3',2':4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylic acid

HRID 1521702Notes

Reaction equation

[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9]3[N:15]=[C:14]([C:16]([O:18]CC)=[O:17])[CH:13]=[CH:12][C:10]=3[CH:11]=[C:3]12.[OH-].[Na+]>C(O)C>[O:1]=[C:2]1[NH:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9]3[N:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:10]=3[CH:11]=[C:3]12

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 6-oxo-7,8,9,10-tetrahydro-6H-pyrido[3′,2′:4,5]pyrrolo[1,2-a][1,4]diazepine-2-carboxylate (1.84 g, 6.73 mmol) in ethanol (30 mL) is added 1N NaOH solution (16.8 mL, 16.8 mmol). The reaction is stirred at 50° C. for 5 h then is cooled to room temperature. The ethanol is removed in vacuo and the aqueous mixture is acidified to pH 5 with 1N hydrochloric acid. The resulting solid is collected by filtration and dried in vacuo at 50° C. to afford the title compound as a tan solid (1.4 g, quantitative). LCMS: 264.63 (M+H+).

Workup

temperaturethen is cooled to room temperature
customThe ethanol is removed in vacuo
filtrationThe resulting solid is collected by filtration
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-29e1cd74c00746dd9ad62ecb64d0dd18
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073926B2

Reaction notes

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