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

HRID 1778111Notes

Reaction equation

HRID 1778111 reaction equation
C1(O[C:8](=[O:22])[NH:9][C:10]2[CH:15]=[C:14]([O:16][CH:17]([CH3:19])[CH3:18])[C:13]([C:20]#[N:21])=[CH:12][N:11]=2)C=CC=CC=1.C(C1C=CC(NC([N:34]2[CH2:40][CH2:39][CH2:38][CH2:37][C:36]3[CH:41]=[CH:42][C:43]([CH:45]([O:48]C)OC)=[N:44][C:35]2=3)=O)=NC=1)#N.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>>[C:20]([C:13]1[C:14]([O:16][CH:17]([CH3:18])[CH3:19])=[CH:15][C:10]([NH:9][C:8]([N:34]2[C:35]3[C:36](=[CH:41][C:42]([CH2:50][N:51]4[CH2:52][CH2:52][N:51]([CH3:53])[CH2:50][C:53]4=[O:54])=[C:43]([CH:45]=[O:48])[N:44]=3)[CH2:37][CH2:38][C@@H:40]2[CH3:39])=[O:22])=[N:11][CH:12]=1)#[N:21]

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 125470513Phenyl (5-cyano-4-isopropoxypyridin-2-yl)carbamate

Product 1

HCID 118036534(S)-N-(5-cyano-4-isopropoxypyridin-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 96 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 brown solid.

Sources & evidence

ORD record
ord-4954b20e3c4e49e9b52d94086c66a9e4
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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