HCID 11995325, compound → 13-Cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylic acid
Reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([O:27]C)=[O:26])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH2:16][CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1.CO.[OH-].[Na+]>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:25]([OH:27])=[O:26])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH2:16][CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1Participants
Procedure
A solution of methyl 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepin-10-carboxylate (45.8 mg, 0.12 mmol) in THF/MeOH (1:2, 3 mL) and 1N aqueous NaOH (0.5 mL) was heated at 50° C. for 5 h. The reaction solution was concentrated to remove volatile organics, neutralized with TFA (0.04 mL) and purified by preparative HPLC (MeOH/H2O with TFA buffer) to yield 13-cyclohexyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepin-10-carboxylic acid (33 mg, 0.092 mmol, 76%) as white solid. 1HNMR (500 MHz, MeOD) δ 8.25 (s, 1H), 7.96 (d, J=8.5 Hz, 1H), 7.79 (dd, J=8.5, 1.2 Hz, 1H), 7.63–7.52 (m, 3H), 7.50–7.46 (m, 1H), 4.44 (br s, 2H), 3.92–3.86 (m, 2H), 3.03 (tt, J=12.4, 3.1 Hz, 1H), 2.21–2.10 (m, 2H), 1.97–1.80 (m, 5H), 1.54–1.36 (m, 2H). LCMS: m/e 361 (M+H)+, ret time 1.88 min, column C, 2 minute gradient, start at 0% B.
Workup
- concentrationThe reaction solution was concentrated
- customto remove volatile organics
- custompurified by preparative HPLC (MeOH/H2O with TFA buffer)
Sources & evidence
- ORD record
- ord-7426eb7f943a48d3af92f96df7c0f1a1
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153848B2
Reaction notes
Loading…