Hydrochloric Acid → N-(3-Pyridinylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 1830093Notes

Reaction equation

HRID 1830093 reaction equation
COC([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][N:8]2[C:16]([C:19]([NH:21][CH2:22][C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[O:20])=[CH:17][CH:18]=[C:7]2[CH2:6]1)=O.C(=O)([O-])[O-].[K+].[K+].O.Cl>CO>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][NH:21][C:19]([C:16]2[N:8]3[C:7]([CH2:6][NH:5][C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[CH2:9]3)=[CH:18][CH:17]=2)=[O:20])[CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 2205365210-(Methoxycarbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Product 1

HCID 22053658N-(3-Pyridinylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10-(methoxycarbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide (5 mmol) of Step B in methanol (50 mL) was treated with potassium carbonate and stirred at room temperature overnight. Water was then added to the solution and the pH adjusted to 6 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous magnesium sulfate, and evaporated to dryness. The residual oil was triturated with ethyl acetate and hexane to yield the title compound as a powder.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customThe residual oil was triturated with ethyl acetate and hexane

Sources & evidence

ORD record
ord-aa39361e44fa45ee9f340f083efb44c7
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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