Diisopropylethylamine → HCID 9798048, compound

HRID 2304700Notes

Reaction equation

HRID 2304700 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH:12]1[CH:13]=[CH:14][N:15]2[CH2:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[NH:18][CH2:17][C:16]=12.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[CH2:21][N:15]2[CH:14]=[CH:13][CH:12]=[C:16]2[CH2:17]1)=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 9798048HCID 9798048, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude 2-chloro-4-fluorobenzoyl chloride (3.68 g) in dichloromethane (25 ml) was added portionwise to a stirred, ice cooled solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (2.76 g), diisopropylethylamine (2.47 g) and dichloromethane (50 ml). After 18 hours at room temperature, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate. The dichloromethane solution was dried with 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 (3.85 g), m.p. 110-112° C.

Workup

  1. washthe reaction mixture was washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialThe dichloromethane solution was dried with 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-042639b4188b431db20994621eecf620
Source dataset
uspto-grants-2002_08
Patent number
US06437006B1

Reaction notes

Loading…