Diisopropylethylamine → HCID 10132459, compound

HRID 1635864Notes

Reaction equation

HRID 1635864 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.[Cl:24][C:25]1[CH:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>ClCCl>[Cl:24][C:25]1[CH:33]=[C:32]([CH:31]=[CH:30][C:26]=1[C:27]([N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]2[CH2:6]1)=[O:28])[C:34]#[N:35]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98130642-chloro-4-cyano-benzoyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 10132459HCID 10132459, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (7.32 g) and diisopropylethylamine (13.6 ml) in dichloromethane (35 ml) was added under nitrogen the cloudy solution of 2-chloro-4-cyanobenzoyl chloride. After one hour at room temperature, the mixture was diluted with dichloromethane and washed sequentially with water, 5% sodium bicarbonate, and 50% saturated brine, After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to afford a crude product (18.0 g). Purification by column chromatography on silica gel (250 g), eluting with 20% ethyl acetate/hexane, followed by 25% ethyl acetate/hexane, yielded the title compound (13.56 g) as a straw yellow foam, MS (EI), m/z: 347 (M)+.

Workup

  1. washwashed sequentially with water, 5% sodium bicarbonate, and 50% saturated brine
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customto afford a crude product (18.0 g)
  5. customPurification by column chromatography on silica gel (250 g)
  6. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3ca897fda5564b98a0a931eb92cf0b7c
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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