Dimethylformamide → (S)-8-chloro-11,12,13,13a-tetrahydro-N-(2-propynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

HRID 867551Notes

Reaction equation

HRID 867551 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=O)[N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]3[CH:22]=[CH:21]N=C3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:27]N(C)C=O.C(N)C#C>O>[Cl:1][C:2]1[C:7]2[CH2:8][N:9]3[CH2:25][CH2:24][CH2:23][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH:18][CH2:22][C:21]#[CH:27])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 239041PropargylamineHCID 54332091(S)-1-[(8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl)carbonyl]imidazole

Product 1

HCID 54413206(S)-8-chloro-11,12,13,13a-tetrahydro-N-(2-propynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 54.7 g (148.7 mmol) of 1-[[(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepin-1-yl]carbonyl]imidazole, 100 ml of N,N-dimethylformamide and 8.60 g (156.1 mmol) of propargylamine is stirred at room temperature overnight. The solution obtained is then poured into 500 ml of water, the resulting suspension is filtered under suction and the filter residue is dried. By recrystallization from methylene chloride and ethyl acetate there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-N-(2-propynyl)-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide of melting point 233°-235°.

Workup

  1. customThe solution obtained
  2. filtrationthe resulting suspension is filtered under suction
  3. customthe filter residue is dried
  4. customBy recrystallization from methylene chloride and ethyl acetate

Sources & evidence

ORD record
ord-780c2366b85b4a7cb96c332db08c6797
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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