Water → HCID 69955128, compound

HRID 1290971Notes

Reaction equation

HRID 1290971 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.C(N(CC)CC)C.[Br:22][C:23]1[CH:31]=[C:30]([NH:32][C:33](=[O:46])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)[CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].O>ClCCl>[Br:22][C:23]1[CH:31]=[C:30]([NH:32][C:33](=[O:46])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=2)[CH:29]=[CH:28][C:24]=1[C:25]([N:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[CH2:10][N:4]2[CH:3]=[CH:2][CH:1]=[C:5]2[CH2:6]1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 53959209HCID 53959209, compound

Product 1

HCID 69955128HCID 69955128, compoundYield 104.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of the product from Reference Example 6, 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.54 g. 2.93 mmol) in dichloromethane (35 ml), under nitrogen, was added triethylamine (0.49 ml, 3.52 mmol). The mixture was cooled to 0° C. before a suspension of the crude 2-bromo-4-[(2-pyridin-2-ylbenzoyl)amino]benzoyl chloride (1.4 g) in dichloromethane (5 ml) was added dropwise. After the addition was complete, the reaction mixture was allowed to warm to room temperature. After 18 hours the reaction mixture was poured into water and sequentially washed with water, saturated aqueous sodium bicarbonate, twice with 10% aqueous acetic acid, once with saturated aqueous sodium bicarbonate and once with water. The organic solution was dried (Na2SO4), filtered and in vacuo to yield a dark purple foam (1.73 g). Purification by flash chromatography on silica gel with hexane-ethyl acetate (1:2) as the mobile phase, followed by concentration in vacuo, resulted in a colorless solid (1.23 g, 75%), m.p. 227.5°-229° C. MS (ESI),m/z: 563 (M+).

Workup

  1. additionwas added dropwise
  2. additionAfter the addition
  3. washsequentially washed with water, saturated aqueous sodium bicarbonate, twice with 10% aqueous acetic acid, once with saturated aqueous sodium bicarbonate and once with water
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. filtrationfiltered and in vacuo

Sources & evidence

ORD record
ord-8bd46fc41162425682f4cdc4b9b04c84
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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