1,1-Dimethoxyethyl(dimethyl)amine → (S)-8-chloro-N-[1-(dimethylamino)ethylidene]-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

HRID 867532Notes

Reaction equation

HRID 867532 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([NH2:18])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.CO[C:25](OC)([N:27]([CH3:29])[CH3:28])[CH3:26]>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]3[CH2:21][CH2:20][CH2:19][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([N:18]=[C:25]([N:27]([CH3:29])[CH3:28])[CH3:26])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 54153267(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Product 1

HCID 54118268(S)-8-chloro-N-[1-(dimethylamino)ethylidene]-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19 g (60 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide are suspended in 110 ml of N,N-dimethylformamide, whereupon the suspension is treated with 17 ml (116 mmol) of N,N-dimethylacetamide dimethyl acetal and the mixture is stirred at 115° for 2.5 hours. The mixture is then cooled to 0°, the product is filtered off under suction, rinsed with N,N-dimethylformamide and diethyl ether and dried at 80° in a high vacuum. There is obtained (S)-8-chloro-N-[1-(dimethylamino)ethylidene]-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamide of decomposition point 289°-291°.

Workup

  1. temperatureThe mixture is then cooled to 0°
  2. filtrationthe product is filtered off under suction
  3. washrinsed with N,N-dimethylformamide and diethyl ether
  4. customdried at 80° in a high vacuum

Sources & evidence

ORD record
ord-b122a7bc10fd4e7bbeadaad2620e9205
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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