6-Amino-4-(2-methoxyethylamino)pyridine-3-carbonitrile → (S)-N-(5-cyano-4-((2-methoxyethyl)amino)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 1778112Notes

Reaction equation

HRID 1778112 reaction equation
N[C:2]1C=C(NCCOC)C(C#N)=CN=1.[C:15]([C:17]1[C:18]([NH:50][CH2:51][CH2:52][O:53][CH3:54])=[CH:19][C:20]([NH:23][C:24]([N:26]2[C:35]3[C:30](=[CH:31][C:32]([CH2:41][N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][C:43]4=[O:49])=[C:33]([CH:36](OC)[O:37]C)[N:34]=3)[CH2:29][CH2:28][CH2:27]2)=[O:25])=[N:21][CH:22]=1)#[N:16]>>[C:15]([C:17]1[C:18]([NH:50][CH2:51][CH2:52][O:53][CH3:54])=[CH:19][C:20]([NH:23][C:24]([N:26]2[C:35]3[C:30](=[CH:31][C:32]([CH2:41][N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][C:43]4=[O:49])=[C:33]([CH:36]=[O:37])[N:34]=3)[CH2:29][CH2:28][C@@H:27]2[CH3:2])=[O:25])=[N:21][CH:22]=1)#[N:16]

Participants

3

Reactant 2

HCID 1180369516-Amino-4-(2-methoxyethylamino)pyridine-3-carbonitrileHCID 1180370081,8-Naphthyridine-1(2H)-carboxamide, N-[5-cyano-4-[(2-methoxyethyl)amino]-2-pyridinyl]-7-(dimethoxymethyl)-3,4-dihydro-6-[(4-methyl-2-oxo-1-piperazinyl)methyl]-

Product 1

HCID 118037040(S)-N-(5-cyano-4-((2-methoxyethyl)amino)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 75 and 268, coupled and deprotected in an analogous manner to intermediate 80 and Example 201. The title compound was obtained as a white solid.

Sources & evidence

ORD record
ord-68e518736d3d4391b913dc06c297ec8a
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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