Diisopropylethylamine → HCID 18917522, compound

HRID 1290944Notes

Reaction equation

HRID 1290944 reaction equation
[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1.C(N(C(C)C)CC)(C)C.[F:38][C:39]1[CH:40]=[CH:41][C:42]([CH3:48])=[C:43]([CH:47]=1)[C:44](Cl)=[O:45]>ClCCl>[CH3:1][N:2]([CH3:28])[CH2:3][CH2:4][N:5]([C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][N:17]3[CH:25]=[CH:26][CH:27]=[C:16]3[CH2:15]2)=[O:13])=[CH:10][N:11]=1)[C:44](=[O:45])[C:43]1[CH:47]=[C:39]([F:38])[CH:40]=[CH:41][C:42]=1[CH3:48]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27373835-Fluoro-2-methylbenzoyl chlorideHCID 18917483HCID 18917483, compound

Product 1

HCID 18917522HCID 18917522, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.75 g of 10-[[6-[2-(dimethylamino)ethylamino]-3-pyridinyl]carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine and 5 ml of diisopropylethylamine in 75 ml of dichloromethane is added (slowly) 0.35 g of 5-fluoro-2-methylbenzoyl chloride in 10 ml of dichloromethane. The mixture is stirred at room temperature for 16 hours and the solution washed well with water. The organic layer is dried (MgSO4) and the solvent removed under vacuum. The residue is purified by column chromatography on silica gel with 30% methanol in chloroform as eluent to give 0.80 g of yellow solid; mass spectrum (CI), 511 (M+1).

Workup

  1. washthe solution washed well with water
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customthe solvent removed under vacuum
  4. customThe residue is purified by column chromatography on silica gel with 30% methanol in chloroform as eluent

Sources & evidence

ORD record
ord-b05585bd3e2a4d9ba8c24c24b6bc1c1b
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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