4-Amino-1-methylpiperidine → 5-Chloro-3,8-dimethyl-N-(1-methyl-4-piperidinyl)-9H-pyrido[2,3-b]indole-7-carboxamide

HRID 2060916Notes

Reaction equation

HRID 2060916 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=O)[C:8]([CH3:14])=[C:7]2[C:3]=1[C:4]1[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:5]=1[NH:6]2.[CH3:20][N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:27][CH:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)=[O:13])[C:8]([CH3:14])=[C:7]2[C:3]=1[C:4]1[CH:18]=[C:17]([CH3:19])[CH:16]=[N:15][C:5]=1[NH:6]2

Participants

3

Reactant 2

HCID 27375314-Amino-1-methylpiperidineHCID 57741423HCID 57741423, compound

Product 1

HCID 161243085-Chloro-3,8-dimethyl-N-(1-methyl-4-piperidinyl)-9H-pyrido[2,3-b]indole-7-carboxamide

Procedure

The title compound was synthesized from 5-chloro-3,8-dimethyl-9H-pyrido[2,3-b]indole-7-carboxylic acid and 1-methylpiperidin-4-amine using an analogous procedure to that described in the preparation of Compound 88. 1H NMR (400 MHz, DMSO-d6 with TFD) δ ppm 1.70-2.2 (m, 4H) 2.53 (br. s., 3H) 2.58 (s, 3H) 2.74-2.82 (m, 3H) 2.80-4.10 (m, 5H) 7.29 (s, 1H) 8.47 (s, 1H) 8.70 (s, 1H). [M+H] calc'd for C20H18N2O2S 371; found, 371.4.

Sources & evidence

ORD record
ord-8707ab16ddc14f00b9222b5d9da8cd47
Source dataset
uspto-grants-2012_10
Patent number
US08278450B2

Reaction notes

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