Diisopropylethylamine → HCID 9799407, compound

HRID 2307358Notes

Reaction equation

HRID 2307358 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=2)[CH:6]=1.[CH:16]1[CH:17]=[CH:18][N:19]2[CH2:25][C:24]3[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=3[NH:22][CH2:21][C:20]=12.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([N:22]3[C:23]4[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=4[CH2:25][N:19]4[CH:18]=[CH:17][CH:16]=[C:20]4[CH2:21]3)=[O:12])=[CH:9][CH:8]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 226054414-(4-Methyl-1H-pyrazol-1-yl)benzoyl chloride

Product 1

HCID 9799407HCID 9799407, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(4-methylpyrazol-1-yl)benzoyl chloride (0.72 g) was added to an ice-cooled solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.60 g) and diisopropylethylamine (0.48 g) in dichloromethane (25 ml). 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 and 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 (0.75 g), m.p. 179-181° C.; MS m/z: 369 (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-3e39c06d4d854330b821e178917dffee
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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