Diisopropylethylamine → HCID 9969337, compound

HRID 2307352Notes

Reaction equation

HRID 2307352 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.[CH3:24][N:25]1[CH:29]=[C:28]([C:30]2[N:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=2)[CH:27]=[N:26]1>ClCCl>[CH3:24][N:25]1[CH:29]=[C:28]([C:30]2[N:35]=[CH:34][C:33]([C:36]([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:37])=[CH:32][CH:31]=2)[CH:27]=[N:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 226054536-(1-methyl-1H-pyrazol-4-yl)pyridine-3-carbonyl chloride

Product 1

HCID 9969337HCID 9969337, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.37 g) and diisopropylethylamine (0.61 g) in dichloromethane (25 ml) was cooled to 0° C. and a solution of 6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-carbonyl chloride in dichloromethane (25 ml) was added portionwise. 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 (0.31 g), m.p. 173-175° C.; MS, m/z: 370.3 (M+H)+.

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-5b24c56935c044c5a2c5ce0d1369580e
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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