Diisopropylethylamine → HCID 10229346, compound

HRID 1270197Notes

Reaction equation

HRID 1270197 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.C1(C2C=CC([C:42]([N:44]3[C:50]4C=CC=C[C:49]=4[CH2:48][N:47]4C(C(O)=O)=CC=[C:46]4[CH2:45]3)=O)=CC=2)CCCCC1.C(N(CC)C(C)C)(C)C.CN1CCCNCC1>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:47]5[CH2:48][CH2:49][CH2:50][N:44]([CH3:42])[CH2:45][CH2:46]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

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 10223535HCID 10223535, compoundHCID 18449085HCID 18449085, compound

Product 1

HCID 10229346HCID 10229346, 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 from 2.5 g of the corresponding acid of Example 22, in the manner of Example 23) was added to a stirred mixture of N,N-diisopropylethyl amine (1.73 g), 4-(dimethylamino)pyridine (0.1 g) and N-methyl homopiperazine (1.52 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 refluxed with the slow addition of hexane to provide the title compound as off-white crystals (0.46 g), m.p. 133–136° C.

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. temperaturethe eluate refluxed with the slow addition of hexane

Sources & evidence

ORD record
ord-85b5d41bf34945509c5232b06b0d5e09
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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