Hydrochloric Acid → HCID 66844632, compound

HRID 1970940Notes

Reaction equation

HRID 1970940 reaction equation
[CH:1]1([C:7]2[CH:31]=[CH:30][CH:29]=[C:28]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][CH:26]=[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:31]=[CH:30][CH:29]=[C:28]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][CH:26]=[N:27][C:13]4=[CH:12][N:11]23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66844863HCID 66844863, compound

Product 1

HCID 66844632HCID 66844632, compoundYield 144.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 10-cyclohexyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylate (34 mg, 0.083 mmol) in THF (1.5 mL) and MeOH (1 mL), was added aq NaOH (1.0N, 0.4 mL, 0.4 mmol). The reaction mixture was heated at 70° C. for 2 h, cooled to rt, neutralized with aq HCl (1.0N, 0.4 mL) and concentrated to dryness. The solid residue was dissolved into MeOH, filtered, concentrated and dried under N2 to yield 10-cyclohexyl-4H-imidazo[1,2-a]indolo[1,2-d][1,4]benzodiazepine-7-carboxylic acid (47 mg, 0.12 mmol) as an off-white solid which was used without further purification. 1H NMR (500 MHz, d6-DMSO) δ 1.04-1.22 (m, 1H), 1.32-1.50 (m, 3H), 1.61-1.77 (m, 2H), 1.84-2.15 (m, 4H), 2.74-2.90 (m, 1H), 5.05 (d, J=15.7 Hz, 1H), 6.00 (d, J=15.7 Hz, 1H), 7.31 (s, 1H), 7.63-7.85 (m, 5H), 7.91-7.99 (m, 2H), 8.37 (s, 1H). LCMS: m/e 398 (M+H)+, ret time 1.87 min.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated to dryness
  3. dissolutionThe solid residue was dissolved into MeOH
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried under N2

Sources & evidence

ORD record
ord-7a94aa8d62a8453294913810aa084057
Source dataset
uspto-grants-2013_04
Patent number
US08431568B2

Reaction notes

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