Water → HCID 54482821, compound

HRID 1940824Notes

Reaction equation

HRID 1940824 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.[CH2:15](N(CC)CC)C.CO[C:24]1[CH:32]=[C:31]([NH:33][C:34](=[O:47])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=2)[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].[OH2:48]>ClCCl>[CH3:15][O:48][C:3]1[N:4]2[C:5]([CH2:6][N:7]([C:26]([C:25]3[CH:29]=[CH:30][C:31]([NH:33][C:34](=[O:47])[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=4[C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=4)=[CH:32][CH:24]=3)=[O:27])[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10]2)=[CH:1][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 53778356HCID 53778356, compound

Product 1

HCID 54482821HCID 54482821, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product from Reference Example 6, 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.405 g. 2.20 mmol) in dichloromethane (30 ml), under nitrogen, was added triethylamine (0.37 ml, 2.64 mmol). The mixture was cooled to 0° C. and a solution of the crude 2-methoxy-4-[(2-pyridin-2-ylbenzoyl)-amino]benzoyl chloride (1.16g) in dichloromethane (30 ml) was added dropwise. After 5 hours the reaction mixture was poured into water. The organic layer was separated and sequentially washed twice with water and aqueous sodium bicarbonate, and once with water. The organic solution was dried (Na2SO4) and concentrated in vacuo to give a marron solid (1.1 g, 94%). Purification by flash chromatography on silica gel with hexane-ethyl acetate-methylene chloride-methanol (3:6:2:0.5) as a mobile phase, followed by concentration in vacuo, resulted in a pale purple solid (0.88 g, 76%), m.p. 138°-140° C. MS (FAB),m/z: 515 (M+H).

Workup

  1. customThe organic layer was separated
  2. washsequentially washed twice with water and aqueous sodium bicarbonate
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0599dac4289e44938acfeb87f171734c
Source dataset
uspto-grants-1997_12
Patent number
US05700796

Reaction notes

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