4-[3-(1-Methyl-pyrrolidin-2-yl)propyl]piperidine → 4,9-Dihydro-3-methyl-4-[[[2-[4-[3-(1-methyl-pyrrolidin-2-yl)propyl]-piperidin-l-yl]ethyl]amino]carbonyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 2351457Notes

Reaction equation

HRID 2351457 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[NH:11][C:10](=[O:18])[C:9]2=[CH:19][S:20][C:21]([CH3:22])=[C:8]12)=[O:6].[CH3:23][N:24]1[CH2:28][CH2:27][CH2:26][CH:25]1[CH2:29][CH2:30][CH2:31][CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>C(OCC)(=O)C.C(O)C>[CH3:22][C:21]1[S:20][CH:19]=[C:9]2[C:10](=[O:18])[NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([C:5]([NH:4][CH2:3][CH2:2][N:35]3[CH2:36][CH2:37][CH:32]([CH2:31][CH2:30][CH2:29][CH:25]4[CH2:26][CH2:27][CH2:28][N:24]4[CH3:23])[CH2:33][CH2:34]3)=[O:6])[C:8]=12

Participants

4

Reactant 2

HCID 198042154-[3-(1-Methyl-pyrrolidin-2-yl)propyl]piperidineHCID 198460264-[[[2-bromo-ethyl]amino]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 543984404,9-Dihydro-3-methyl-4-[[[2-[4-[3-(1-methyl-pyrrolidin-2-yl)propyl]-piperidin-l-yl]ethyl]amino]carbonyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 18%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 109 from 4-[[[2-bromo-ethyl]amino]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 4-[3-(1-methyl-pyrrolidin-2-yl)propyl]piperidine in a yield of 18% of theory. Colourless crystals, m.p. 145°-146° C. (from ethyl acetate/ethanol). RF =0.5 (TLC investigation as in Example 114).

Sources & evidence

ORD record
ord-fc4226085c3b40ceac1e05ebfcd866cd
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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