Diisopropylethylamine → HCID 10144665, compound

HRID 1270194Notes

Reaction equation

HRID 1270194 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.Cl.[C:42]1(C)[C:43]([C:48]([N:50]2[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]2)=O)=[CH:44][CH:45]=[CH:46][CH:47]=1>CN(C)C1C=CN=CC=1.ClCCl>[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]([N:53]5[CH2:52][CH2:51][N:50]([C:48]6[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=6[CH3:42])[CH2:55][CH2:54]5)=[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

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760445Piperazin-1-yl-o-tolyl-methanone hydrochlorideHCID 18449085HCID 18449085, compound

Product 1

HCID 10144665HCID 10144665, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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 (0.5 g) was added to a stirred mixture of N,N-diisopropylethyl amine (0.47 g), 4-(2-toluoyl)piperazine hydrochloride (0.51 g) and 4-(dimethylamino)pyridine (0.05 g) in dichloromethane (25 mL). After stirring overnight at room temperature the reaction mixture was washed with water and saturated aqueous sodium bicarbonat, and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol®. Refluxing the eluate with the gradual addition of hexane resulted in crystallization of the desired title compound (0.46 g) as colorless crystals, m.p. 141–143° C.

Workup

  1. washwas washed with water and saturated aqueous sodium bicarbonat
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered through a short column of Magnesol®
  4. temperatureRefluxing the eluate
  5. additionwith the gradual addition of hexane

Sources & evidence

ORD record
ord-75e8ce66a8c94d6b8606d9317d092992
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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