Tetrafluoro-m-phenylenediamine dihydrochloride → 5,11-Dihydro-11-[[[2-[4-[4-(piperidin-1-yl)butyl]-piperidin-1-yl]ethyl]amino]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one dihydrochloride

HRID 2351425Notes

Reaction equation

HRID 2351425 reaction equation
[Cl:1][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[N:20]1([CH2:26][CH2:27][CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][NH2:38])[CH2:32][CH2:31]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:51].Cl>>[ClH:1].[ClH:51].[N:20]1([CH2:26][CH2:27][CH2:28][CH2:29][CH:30]2[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][NH:38][C:2]([N:4]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[C:8](=[O:15])[NH:7][C:6]4[CH:16]=[CH:17][CH:18]=[N:19][C:5]3=4)=[O:3])[CH2:32][CH2:31]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 19845995HCID 19845995, compound

Product 1

HCID 198460145,11-Dihydro-11-[[[2-[4-[4-(piperidin-1-yl)butyl]-piperidin-1-yl]ethyl]amino]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one dihydrochlorideYield 40%

Procedure

Prepared analogously to Example 46 from 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 2-[4-[4-(piperidin-1-yl)butyl]-piperidin-1-yl]ethanamine in a yield of 40% of theory. The colourless dihydrochloride melted at 231°-233° C.

Sources & evidence

ORD record
ord-ed29a396f8b44f5f8139cc01967b251a
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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