Diisopropylethylamine → HCID 9819979, compound

HRID 2307363Notes

Reaction equation

HRID 2307363 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][CH2:6][C:5]=12.C(N(C(C)C)CC)(C)C.Cl.[N:25]1([C:30]2[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=2)[CH:29]=[CH:28][N:27]=[CH:26]1>CN(C)C1C=CN=CC=1.ClCCl>[N:25]1([C:30]2[CH:31]=[CH:32][C:33]([C:34]([N:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH2:10][N:4]4[CH:3]=[CH:2][CH:1]=[C:5]4[CH2:6]3)=[O:35])=[CH:37][CH:38]=2)[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 22605439HCID 22605439, compound

Product 1

HCID 9819979HCID 9819979, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]-benzodiazepine (0.75), diisopropylethylamine (1.20 g), and 4-dimethylaminopyridine (0.1 g) in dichloromethane (50 ml) was added 4-(imidazol-1-yl)benzoyl chloride hydrochloride (1.12 g). After stirring at room temperature for 18 hours, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried over anhydrous sodium sulfate, filtered through a short column of hydrous sodium magnesium silicate, and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (0.57 g), m.p. 171-172° C.; MS, m/z: 354 (M+H)+.

Workup

  1. washthe reaction mixture was washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered through a short column of hydrous sodium magnesium silicate
  4. washfurther eluted with several volumes of dichloromethane
  5. concentrationThe combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization
  6. temperatureAfter cooling
  7. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-fcbfa1360a83460e86584dd3aa2f1a86
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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