Hydrochloric Acid → HCID 10119684, compound

HRID 1270179Notes

Reaction equation

HRID 1270179 reaction equation
[CH:1]1([C:7]2[CH:41]=[CH:40][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[C:21]([C:24]([O:26]C)=[O:25])[CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:28]([C:31]([N:33]5[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]5)=[O:32])=[CH:29][CH:30]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([C:7]2[CH:41]=[CH:40][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[C:21]([C:24]([OH:26])=[O:25])[CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:28]([C:31]([N:33]5[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]5)=[O:32])=[CH:29][CH:30]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10144104HCID 10144104, compound

Product 1

HCID 10119684HCID 10119684, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the methyl 10-(4-cyclohexylbenzoyl)-3-[(4-methyl-1-piperazinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-8-carboxylate of Example 1, Step D (1.1 g, 1.93 mmol) in ethanol (10 mL) was added 2.5 N sodium hydroxide (1.5 equiv.) and the reaction mixture was stirred overnight at room temperature. The solution was neutralized by the addition of one equivalent of 2 N hydrochloric acid and the solvent was removed in vacuo. The residue was extracted with dichloromethane, filtered and the solvent removed in vacuo. The residue was then chromatographed on silica gel eluting with 10% methanol in dichloromethane to provide the title product as a white crystalline solid, m.p. 195–210° C.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe residue was extracted with dichloromethane
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe residue was then chromatographed on silica gel eluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-a9e8cd843d6c49ad8afe50072ed5f125
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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