Hydrochloric Acid → 10-((aminosulfonyl)carbamoyl)-13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylic acid

HRID 1986008Notes

Reaction equation

HRID 1986008 reaction equation
[NH2:1][S:2]([NH:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[C:13]3[C:19]4[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=4[CH:17]=[C:16]([C:26]([O:28]C)=[O:27])[CH2:15][N:14]3[C:30]=2[CH:31]=1)=[O:7])(=[O:4])=[O:3].CO.[OH-].[Na+].Cl>CO.[H][H]>[NH2:1][S:2]([NH:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]2[C:12]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[C:13]3[C:19]4[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=4[CH:17]=[C:16]([C:26]([OH:28])=[O:27])[CH2:15][N:14]3[C:30]=2[CH:31]=1)=[O:7])(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57559091methyl 10-((aminosulfonyl)carbamoyl)-13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate

Product 1

HCID 5755909210-((aminosulfonyl)carbamoyl)-13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 178502592HCID 178502592, compoundSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 10-((aminosulfonyl)carbamoyl)-13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylate (725 mg, 1.39 mmol) was dissolved into MeOH//THF (1:1, 16 mL) and treated with 1M aqueous NaOH (3 mL). The reaction mixture was stirred and heated at 60° C. for 0.5 h and cooled to rt. The reaction solution was diluted with MeOH/H2 O (2:1, 15 mL), neutralized with 1M aqueous HCl (3 mL) and concentrated to remove organic solvents. The resultant solids were collected by filtration, washed with H2O and dried under vacuum to yield 10-((aminosulfonyl)carbamoyl)-13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6-carboxylic acid (650 g, 1.3 mmol, 92%) as a bright yellow solid which was used without further purification. 1HNMR (300 MHz, CDCl3) δ 1.16-2.22 (m, 10H), 2.82-2.96 (m, 1H), 3.94 (s, 3H), 4.07-4.29 (m, 1H), 5.57-5.80 (m, 1H), 7.14-7.23 (m, 2H), 7.55-7.63 (m, 2H), 7.88-7.94 (m 2H), 8.18 (s, 1H). LCMS: m/e 510 (M+H)+, ret time 2.85 min, column B, 4 minute gradient.

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. customto remove organic solvents
  4. filtrationThe resultant solids were collected by filtration
  5. washwashed with H2O
  6. customdried under vacuum

Sources & evidence

ORD record
ord-0eee438bf00f41a383771a6b23c25416
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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