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

HRID 2351456Notes

Reaction equation

HRID 2351456 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].[N:23]1([CH2:30][CH2:31][CH2:32][CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.N>ClCCl.C1CCCCC1.CO>[N:23]1([CH2:30][CH2:31][CH2:32][CH:33]2[CH2:38][CH2:37][N:36]([CH2:2][CH2:3][NH:4][C:5]([N:7]3[C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[NH:11][C:10](=[O:18])[C:9]4=[CH:19][S:20][C:21]([CH3:22])=[C:8]34)=[O:6])[CH2:35][CH2:34]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 198460264-[[[2-bromo-ethyl]amino]carbonyl]-4,9-dihydro-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneHCID 198460684-[3-(hexahydro-1H-azepin-l-yl)propyl]piperidine

Product 1

HCID 538078514,9-Dihydro-4-[[[2-[4-[3-(hexahydro-1H-azepin-1-yl)propyl]-piperidin-l-yl]ethyl]amino]carbonyl]-3-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-oneYield 29%

Reagents, catalysts & solvents 1

HCID 69163855HCID 69163855, compoundSolvent

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-(hexahydro-1H-azepin-l-yl)propyl]piperidine in a yield of 29% of theory. Colourless crystals m.p. 144°-145° C. RF =0.5 (Macherey-Nagel, PolygramRSIL G/UV254, pre-coated plastic sheets for TLC; eluant: dichloromethane/cyclohexane/methanol/conc. ammonia 68/15/15/2 v/v).

Sources & evidence

ORD record
ord-8171cb111d824dd79ecffa8bcc522215
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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