Dimethylformamide → 11-[[[2-[4-[4-(Diethylamino)butyl]-piperidin-l-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351454Notes

Reaction equation

HRID 2351454 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6].[CH2:23]([N:25]([CH2:36][CH3:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH3:24].CN(C)C=O>C(OCC)(=O)C>[CH2:36]([N:25]([CH2:23][CH3:24])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]1[CH2:31][CH2:32][N:33]([CH2:2][CH2:3][NH:4][C:5]([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)=[O:6])[CH2:34][CH2:35]1)[CH3:37]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 100819184-Piperidinebutanamine, N,N-diethyl-HCID 1984600611-[[[2-bromo-ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Product 1

HCID 5436358811-[[[2-[4-[4-(Diethylamino)butyl]-piperidin-l-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared analogously to Example 109 from 11-[[[2-bromo-ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 4-[4-(diethylamino)butyl]-piperidine, but using dimethylformamide instead of acetonitrile, in a yield of 60% of theory. Colourless crystals, m.p. 167° C. (ethyl acetate).

Sources & evidence

ORD record
ord-7e645da9d6f54f3b8d01975bf8f99902
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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