Diisopropylethylamine → HCID 9842958, compound

HRID 2307360Notes

Reaction equation

HRID 2307360 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=2)[N:3]=1.[CH:17]1[CH:18]=[CH:19][N:20]2[CH2:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[NH:23][CH2:22][C:21]=12.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([N:23]3[C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[CH2:26][N:20]4[CH:19]=[CH:18][CH:17]=[C:21]4[CH2:22]3)=[O:13])=[CH:10][CH:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 128534534-(3,5-Dimethyl-1H-pyrazol-1-yl)benzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 9842958HCID 9842958, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(3,5-dimethylpyrazol-1-yl)benzoyl chloride (0.75 g) was added to an ice-cooled solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.55 g) and diisopropylethylamine (0.42 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 title compound (0.79 g) was obtained as an amorphous solid, MS m/z: 383 (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

Sources & evidence

ORD record
ord-77755f1a161a4c32b2ba7635d1f4cd51
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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