Hydrochloric Acid → HCID 66844545, compound

HRID 1970942Notes

Reaction equation

[CH:1]1([C:7]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:8]=2[CH:9]=[C:10]2[C:16]4[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[CH:19]=[CH:20][C:15]=4[N:14]4[CH2:25][C:26]([CH3:28])=[N:27][C:13]4=[CH:12][N:11]23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]1([C:7]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:8]=2[CH:9]=[C:10]2[C:16]4[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[CH:19]=[CH:20][C:15]=4[N:14]4[CH2:25][C:26]([CH3:28])=[N:27][C:13]4=[CH:12][N:11]23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 10-cyclohexyl-2-methyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylate (74 mg, 0.17 mmol) in THF (3 mL) and MeOH (1.5 mL) was added aq NaOH (1.0N, 0.8 mL, 0.8 mmol). The reaction mixture was heated at 70° C. for 2 h, cooled to rt, neutralized with aq. HCl (1.0N, 0.8 mL, 0.8 mmol) and concentrated to dryness. The solid residue was dissolved into MeOH/DCM, insoluble material was removed by filtration and the filtrate was concentrated and dried under N2 to yield crude 10-cyclohexyl-2-methyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylic acid (60 mg, 0.15 mmol, 86%) as an off-white solid which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 1.16-1.56 (m, 4H), 1.72-2.22 (m, 6H), 2.31 (s, 3H), 2.80-3.01 (m, 1H), 5.12 (d, J=16.1 Hz, 1H), 5.91 (d, J=16.1 Hz, 1H), 7.62 (s, 1H), 7.72-7.86 (m, 5H), 7.97 (d, J=8.8 Hz, 1H), 8.39 (s, 1H). LCMS: m/e 412 (M+H)+, ret time 1.65 min.

Workup

temperaturecooled to rt
concentrationconcentrated to dryness
dissolutionThe solid residue was dissolved into MeOH/DCM, insoluble material
customwas removed by filtration
concentrationthe filtrate was concentrated
customdried under N2

Sources & evidence

ORD record: ord-2cb60c453e3247469dd16bd2162c5a8c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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