Diisopropylethylamine → HCID 18917519, compound

HRID 1940799Notes

Reaction equation

HRID 1940799 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:12][N:13]([CH3:40])[CH2:14][CH2:15][CH2:16][NH:17][C:18]1[N:23]=[CH:22][C:21]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][N:29]3[CH:37]=[CH:38][CH:39]=[C:28]3[CH2:27]2)=[O:25])=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH3:40][N:13]([CH3:12])[CH2:14][CH2:15][CH2:16][N:17]([C:18]1[CH:19]=[CH:20][C:21]([C:24]([N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][N:29]3[CH:37]=[CH:38][CH:39]=[C:28]3[CH2:27]2)=[O:25])=[CH:22][N:23]=1)[C:7](=[O:8])[C:6]1[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 18917552HCID 18917552, compound

Product 1

HCID 18917519HCID 18917519, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6.35 g of 5-fluoro-2-methylbenzoyl chloride in 10 ml of dichloromethane is added to a solution of 2 mmol of 10-[[6-[3-(dimethylamino)-propylamino]-3-pyridinyl]carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 5 ml of diisopropylethylamine in 75 ml of dichloromethane. The solution is stirred 16 hours at room temperature, washed with water, dried (MgSO4) and the solvent removed. The residue is purified by column chromatography over silica gel with 30% methanol in chloroform as eluent to give 0.75 g of solid; mass spectrum (CI) 525 (M+1).

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed
  4. customThe residue is purified by column chromatography over silica gel with 30% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-7e27f598bcb7422ea383f49702f27f3c
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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