Sodium Hydroxide → HCID 66844431, compound

HRID 1970938Notes

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[CH:25]=[N:26][N:27]([CH3:28])[C:13]4=[CH:12][N:11]23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>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[CH:25]=[N:26][N:27]([CH3:28])[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-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxylate (173 mg, 0.406 mmol) in THF (7 mL) and MeOH (3.5 mL), was added aq NaOH (1.0N, 1.8 mL, 1.8 mmol). The reaction mixture was heated at 70° C. for 2 h and the solvents were removed. The resulting white solid residue was washed with water, isolated by centrifuge and dried under N2 to yield 10-cyclohexyl-1-methyl-4H-indolo[1,2-d][1,2,4]triazolo[4,3-a][1,4]benzodiazepine-7-carboxylic acid (132 mg, 0.320 mmol, 79%) as a white solid, which was used without further purification. 1H NMR (500 MHz, d6-DMSO) δ 1.13-1.24 (m, 1H), 1.35-1.51 (m, 3H), 1.66-1.75 (m, 2H), 1.85-2.08 (m, 4H), 2.48 (s, 3H), 2.79-2.89 (m, 1H), 4.90 (d, J=15.6 Hz, 1H), 5.80 (d, J=15.6 Hz, 1H), 7.65-7.72 (m, 5H), 7.78-7.83 (m, 1H), 8.15 (s, 1H). LCMS: m/e 413 (M+H)+, ret time 2.01 min.

Workup

customthe solvents were removed
washThe resulting white solid residue was washed with water
customisolated by centrifuge
customdried under N2

Sources & evidence

ORD record: ord-5da925e3506242cf9a1bae6ed7dd90a1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431568B2

Reaction notes

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