Water → HCID 54482821, compound

HRID 1417974Notes

Reaction equation

HRID 1417974 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 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 (1.16 g) 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 and dried (Na2SO4). The material was filtered and concentrated in vacuo to yield a marron solid (1.1 g). Purification by flash chromatography on silica gel with hexane-ethyl acetate-methlyene chloride, methanol (3:6:2:0.5) as a mobile phase, followed by concentration under vacuum, resulted in a pale purple solid (0.88 g), 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 materialonce with water and dried (Na2SO4)
  4. filtrationThe material was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df1d65f3f55a4a61a2df95f76073401f
Source dataset
uspto-grants-1999_03
Patent number
US05880122

Reaction notes

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