Diisopropylethylamine → 10-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

HRID 2215149Notes

Reaction equation

HRID 2215149 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(CC)C(C)C)(C)C.[Cl:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][N:26]=1>ClCCl>[Cl:24][C:25]1[N:26]=[CH:27][C:28]([C:29]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:30])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepine

Product 1

HCID 2194772510-[(6-Chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (100 mmol) and N,N-diisopropylethyl amine (130 mmol) in dichloromethane (500 mL) was cooled to 0° C. 6-Chloronicotinoyl chloride (130 mmol) was added dropwise under nitrogen. The solution was stirred for one hour as it returned to room temperature. The reaction mixture was filtered through a sica gel pad, washed with 0.5 N sodium hydroxide and water, dried over anhydrous magnesium sulfate. The solution was again filtered through a silica gel pad and evaporated to dryness in vacuo. The residual oil crystallized from diethyl ether to provide the title compound as a colorless crystalline solid, m.p. 165–167° C.

Workup

  1. customreturned to room temperature
  2. filtrationThe reaction mixture was filtered through a sica gel pad
  3. washwashed with 0.5 N sodium hydroxide and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was again filtered through a silica gel pad
  6. customevaporated to dryness in vacuo
  7. customThe residual oil crystallized from diethyl ether

Sources & evidence

ORD record
ord-0c0d08dab9f24496894209294e00d23f
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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