N-(3-(7-amino-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-5-yl)phenyl)-cyclopropanecarboxamide → 3-(7-(cyclopropanecarboxamido)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-5-yl)-N-cyclopropylbenzamide

HRID 1642587Notes

Reaction equation

HRID 1642587 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]2[C:5]([C:6]3[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:7]=3[NH:8]2)=[C:4]([C:18]2[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=2)[C:21]([NH:23][CH:24]2[CH2:26][CH2:25]2)=[O:22])[CH:3]=1.NC1C(OC)=C2C(C3C=C(C)C=NC=3N2)=C(C2C=C(N[C:54]([CH:56]3[CH2:58][CH2:57]3)=[O:55])C=CC=2)C=1>>[CH:56]1([C:54]([NH:1][C:2]2[C:10]([O:11][CH3:12])=[C:9]3[C:5]([C:6]4[CH:16]=[C:15]([CH3:17])[CH:14]=[N:13][C:7]=4[NH:8]3)=[C:4]([C:18]3[CH:19]=[C:20]([CH:27]=[CH:28][CH:29]=3)[C:21]([NH:23][CH:24]3[CH2:26][CH2:25]3)=[O:22])[CH:3]=2)=[O:55])[CH2:58][CH2:57]1

Participants

3

Reactant 2

HCID 58880064N-(3-(7-amino-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-5-yl)phenyl)-cyclopropanecarboxamideHCID 588801443-(7-amino-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-5-yl)-N-cyclopropylbenzamide

Product 1

HCID 588801293-(7-(cyclopropanecarboxamido)-8-methoxy-3-methyl-9H-pyrido[2,3-b]indol-5-yl)-N-cyclopropylbenzamide

Procedure

The title compound was prepared from Compound 244 by using an analogous procedure to that outlined in the preparation of Compound 241. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.55 (m, 2 H) 0.68 (m, 2 H) 0.81 (br. m, 4 H) 2.17 (m, 1 H) 2.23 (s, 3 H) 2.87 (m, 1 H) 3.94 (s, 3 H) 7.40 (s, 1 H) 7.63 (t, J=7.71 Hz, 1 H) 7.72-7.71 (m, 2H) 7.94 (d, J=7.58 Hz, 1 H) 8.01 (s, 1 H) 8.21 (d, J=1.77 Hz, 1 H) 8.54 (d, J=4.04 Hz, 1 H) 9.84 (s, 1 H) 12.00 (s, 1 H); [M+H] calc'd for C27H27N4O3, 455.2; found, 455.4.

Sources & evidence

ORD record
ord-3acd3557280e4fa1aa7507d62940a035
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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