Dimethylformamide → (S)-N-(5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)-7-formyl-2-methyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778110Notes

Reaction equation

HRID 1778110 reaction equation
C1(O[C:8](=[O:23])[NH:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])[C:13]([C:21]#[N:22])=[CH:12][N:11]=2)C=CC=CC=1.C(C1C=CC(NC([N:35]2[CH2:41][CH2:40][CH2:39][CH2:38][C:37]3[CH:42]=[CH:43][C:44]([CH:46]([O:49]C)OC)=[N:45][C:36]2=3)=O)=NC=1)#N.[CH3:51][N:52]([CH:54]=[O:55])[CH3:53]>>[C:21]([C:13]1[C:14]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:15][C:10]([NH:9][C:8]([N:35]2[C:36]3[C:37](=[CH:42][C:43]([CH2:51][N:52]4[CH2:53][CH2:53][N:52]([CH3:54])[CH2:51][C:54]4=[O:55])=[C:44]([CH:46]=[O:49])[N:45]=3)[CH2:38][CH2:39][C@@H:41]2[CH3:40])=[O:23])=[N:11][CH:12]=1)#[N:22]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 118037151N-(5-cyanopyridin-2-yl)-2-(dimethoxymethyl)-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxamideHCID 125470569Phenyl (5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)carbamate

Product 1

HCID 118036665(S)-N-(5-cyano-4-(2-methoxyethoxy)pyridin-2-yl)-7-formyl-2-methyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Procedure

From intermediates 108 and 268, coupled and deprotected in an analogous manner to intermediate 236, but using DMF instead of THF, and Example 201. The title compound was obtained as a light yellow-brown solid.

Sources & evidence

ORD record
ord-67dfb88aeb8f4121874dfd0f4b79f165
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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