P-Anisidine → HCID 10164916, compound

HRID 1270196Notes

Reaction equation

HRID 1270196 reaction equation
[CH:1]1([C:7]2[CH:31]=[CH:30][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27](Cl)=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[CH3:41][O:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1>ClCCl>[CH3:41][O:42][C:43]1[CH:49]=[CH:48][C:46]([NH:47][C:27]([C:24]2[N:16]3[C:15]([CH2:14][N:13]([C:11](=[O:12])[C:10]4[CH:9]=[CH:8][C:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)=[CH:31][CH:30]=4)[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17]3)=[CH:26][CH:25]=2)=[O:28])=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 81531DiisopropylethylamineHCID 18449085HCID 18449085, compound

Product 1

HCID 10164916HCID 10164916, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 10-(4-cyclohexyl-benzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbonyl chloride prepared in the manner of Example 23 (1.0 g) was added to a stirred mixture of N,N-diisopropylethyl amine (0.31 g) and 4-methoxy aniline (0.35 g) in dichloromethane (25 mL). After stirring overnight at room temperature the reaction mixture was washed with water and saturated aqueous sodium bicarbonate, and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® and the eluate evaporated to dryness to provide the desired title compound (1.0 g) as an off-white amorphous solid.

Workup

  1. washwas washed with water and saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered through a short column of Magnesol®
  4. customthe eluate evaporated to dryness

Sources & evidence

ORD record
ord-c116538f044f4c55912722d863d69f08
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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