[5-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indol-7-yl]-(4-methyl-piperazin-1-yl)-methanone → 5-(benzylthio)-N-(2-(dimethylamino)ethyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxamide

HRID 1642556Notes

Reaction equation

HRID 1642556 reaction equation
[CH2:1]([S:8][C:9]1[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[C:14]2[C:10]=1[C:11]1[CH:24]=[C:23]([CH3:25])[CH:22]=[N:21][C:12]=1[NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(S(C1C=C(C2C=C([C:46]([N:48]3[CH2:53]C[N:51](C)[CH2:50][CH2:49]3)=O)C=C3C=2C2C=C(C)C=NC=2N3)C=CC=1)(=O)=O)C>>[CH2:1]([S:8][C:9]1[CH:17]=[C:16]([C:18]([NH:51][CH2:50][CH2:49][N:48]([CH3:53])[CH3:46])=[O:20])[CH:15]=[C:14]2[C:10]=1[C:11]1[CH:24]=[C:23]([CH3:25])[CH:22]=[N:21][C:12]=1[NH:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 25016995[5-(3-Ethanesulfonyl-phenyl)-3-methyl-9H-pyrido[2,3-b]indol-7-yl]-(4-methyl-piperazin-1-yl)-methanoneHCID 588801485-(benzylthio)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxylic acid

Product 1

HCID 250172585-(benzylthio)-N-(2-(dimethylamino)ethyl)-3-methyl-9H-pyrido[2,3-b]indole-7-carboxamide

Procedure

The title compound was synthesized from Compound 150 using an analogous procedure to that described in the preparation of Compound 140. 1H NMR (400 MHz, MeOD) δ ppm 2.53 (s, 3 H) 3.02 (s, 6 H) 3.43 (t, J=5.81 Hz, 2 H) 3.82 (t, J=5.81 Hz, 2 H) 4.42 (s, 2 H) 7.16-7.26 (m, 3 H) 7.31 (d, J=7.83 Hz, 2 H) 7.82 (d, J=1.26 Hz, 1 H) 7.96 (s, 1 H) 8.30 (s, 1 H) 8.80 (s, 1 H) [M+H] calc'd for C24H26N4OS, 419; found, 419.

Sources & evidence

ORD record
ord-fdbe142e918243fd88edef427878c446
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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