Diisopropylethylamine → HCID 9950480, compound

HRID 1635846Notes

Reaction equation

HRID 1635846 reaction equation
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH:15]1[CH:16]=[CH:17][N:18]2[CH2:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[NH:21][CH2:20][C:19]=12.C(N(C(C)C)CC)(C)C>ClCCl>[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([N:21]3[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=4[CH2:24][N:18]4[CH:17]=[CH:16][CH:15]=[C:19]4[CH2:20]3)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27764744-(1H-pyrazol-1-yl)benzoyl chlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 9950480HCID 9950480, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(pyrazol-1-yl)benzoyl chloride (0.75 g) was added to a solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.61 g) and diisopropylethylamine (0.47 g) in dichloromethane (25 ml). After 18 hours at room temperature, the reaction mixture was washed with water and a saturated aqueous sodium bicarbonate solution. 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 (0.90 g), m.p. 179-181° C.

Workup

  1. washthe reaction mixture was washed with water
  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-ff35edacc95e4be99e8dd0cce62746ff
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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