Hydrochloric Acid → 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 1453375Notes

Reaction equation

HRID 1453375 reaction equation
[OH-].[Na+].[CH:3]1[C:13]2[C:12]3=[CH:14][C:15]4[CH:16]=[CH:17][C:18]([C:21]([O:23]C)=[O:22])=[CH:19][C:20]=4[N:11]3[CH2:10][CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl>C1COCC1.CO>[CH:3]1[C:13]2[C:12]3=[CH:14][C:15]4[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[CH:19][C:20]=4[N:11]3[CH2:10][CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68832135methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate

Product 1

HCID 666396797H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Added 1M NaOH (aq.) (0.5 mL, 0.5 mmol) to a solution of methyl 7H-indolo[2,1-a][2]benzazepine-10-carboxylate, 13-cyclohexyl-3-methoxy-6-[[[2-(methylamino)-2-oxoethyl]amino]carbonyl]- (140 mg, 0.27 mmol) in THF/MeOH (1:1, 3 mL) and heated the reaction mixture in a sealed tube with microwave irradiation at 80° C. for 20 min., then at 85° C. for 10 min. The reaction was cooled, neutralized with 1M HCl (aq.) (0.5 mL, 0.5 mmol) and concentrated to remove organic solvents. The residue was slurried with H2O and the solids were collected by filtration, flushed with H2O and dried to yield 7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid, 13-cyclohexyl-3-methoxy-6-[[[2-(methylamino)-2-oxoethyl]amino]carbonyl]- (123 mg, 0.25 mmol, 90%) as a yellow solid. 1HNMR (500 MHz, CD3OD) δ 8.30 (s. 1H), 7.87 (d, J=8.5 Hz, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.62 (s, 1H), 7.60 (d, J=8.5 Hz, 1H), 7.20 (d, J=8.5 Hz, 1H), 7.15 (s, 1H), 5.74-5.60 (m, 1H), 4.24-4.11 (m, 1H), 4.02-3.88 (m, 2H), 3.95 (s, 3H), 2.95-2.84 (m, 1H), 2.75 (s, 3H), 2.22-1.17 (m, 10H). LCMS: m/e 500 (M−H)−, ret time 1.38 min, column A, 3 minute gradient.

Workup

  1. temperatureheated the reaction mixture in a sealed tube
  2. customwith microwave irradiation at 80° C. for 20 min.
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. customto remove organic solvents
  6. filtrationthe solids were collected by filtration
  7. customflushed with H2O
  8. customdried

Sources & evidence

ORD record
ord-63a46c2de20846acbbe629425d4019df
Source dataset
uspto-grants-2009_01
Patent number
US07473688B2

Reaction notes

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