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

HRID 1778108Notes

Reaction equation

HRID 1778108 reaction equation
C1(O[C:8](=[O:24])[NH:9][C:10]2[CH:15]=[C:14]([O:16][C@H:17]([CH3:21])[CH2:18][O:19][CH3:20])[C:13]([C:22]#[N:23])=[CH:12][N:11]=2)C=CC=CC=1.C(C1C=CC(NC([N:36]2C[CH2:41][CH2:40][CH2:39][C:38]3[CH:43]=[CH:44][C:45]([CH:47]([O:50]C)OC)=[N:46][C:37]2=3)=O)=NC=1)#N.[CH3:52][N:53]([CH:55]=[O:56])[CH3:54]>>[C:22]([C:13]1[C:14]([O:16][C@H:17]([CH3:21])[CH2:18][O:19][CH3:20])=[CH:15][C:10]([NH:9][C:8]([N:36]2[C:37]3[C:38](=[CH:43][C:44]([CH2:52][N:53]4[CH2:54][CH2:54][N:53]([CH3:55])[CH2:52][C:55]4=[O:56])=[C:45]([CH:47]=[O:50])[N:46]=3)[CH2:39][CH2:40][CH2:41]2)=[O:24])=[N:11][CH:12]=1)#[N:23]

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 131734794(R)-phenyl (5-cyano-4-((1-methoxypropan-2-yl)oxy)pyridin-2-yl)carbamate

Product 1

HCID 118036293(R)-N-(5-cyano-4-((1-methoxypropan-2-yl)oxy)pyridin-2-yl)-7-formyl-6-((4-methyl-2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Procedure

From intermediates 145 and 81, coupled in an analogous manner to intermediate 236, but using DMF instead of THF, and deprotected in an analagous manner to Example 201. The title compound was obtained as an off-white solid.

Sources & evidence

ORD record
ord-606bc842ff6646f08f009e48ac2348c7
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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