Diisopropylethylamine → HCID 18917507, compound

HRID 1735255Notes

Reaction equation

HRID 1735255 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[C:4]([Cl:24])[CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:34][C:35]1[C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=[CH:37][N:36]=1>C(Cl)Cl>[CH:21]1[CH:20]=[CH:19][N:11]2[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:6]([C:5]3[CH:22]=[CH:23][C:2]([NH:1][C:41]([C:40]4[C:35]([CH3:34])=[N:36][CH:37]=[CH:38][CH:39]=4)=[O:42])=[CH:3][C:4]=3[Cl:24])=[O:7])[CH2:9][C:10]=12

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10806897HCID 10806897, compoundHCID 129025982-Methylpyridine-3-carbonyl chloride

Product 1

HCID 18917507HCID 18917507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.1 g of 10, 11-dihydro-10-(4-amino-2-chlorobenzoyl)-5H-pyrrolo[2, 1-c][1, 4]benzodiazepine and 3 ml of N,N-diisopropylethylamine in 100 ml of methylene chloride is stirred while a solution of 600 mg of 2-methylpyridine-3-carbonyl chloride in 15 ml of methylene chloride is added slowly. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is quenched with water and the organic layer washed with water, dried(MgSO4), filtered and evaporated in vacuo to a residue. The product is purified by column chromatography on silica gel by elution with 1:1 ethyl acetate:hexane to give the desired product as a pale yellow residue. M+ =456.

Workup

  1. additionis added slowly
  2. customThe reaction mixture is quenched with water
  3. washthe organic layer washed with water, dried(MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo to a residue
  6. customThe product is purified by column chromatography on silica gel by elution with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-c937ac4338d8488e8dc09e3a1b35f864
Source dataset
uspto-grants-1996_07
Patent number
US05536718

Reaction notes

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