Methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate → Methyl 3-[(3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(methyloxy)-1-piperidinyl]-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanoate

HRID 15364Notes

Reaction equation

HRID 15364 reaction equation
CC([N:5]([C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[O:15][CH3:16])[C:6](=[O:8])[O-:7])(C)C.[F:17][C:18]1[CH:19]=[N:20][C:21]2[C:26]([C:27]=1[C:28](=[CH2:33])[C:29]([O:31][CH3:32])=[O:30])=[N:25][C:24]([O:34][CH3:35])=[CH:23][CH:22]=2>>[CH3:18][C:27]([O:7][C:6]([NH:5][C@H:9]1[CH2:14][CH2:13][N:12]([CH2:33][CH:28]([C:27]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:34][CH3:35])[N:25]=3)[N:20]=[CH:19][C:18]=2[F:17])[C:29]([O:31][CH3:32])=[O:30])[CH2:11][C@H:10]1[O:15][CH3:16])=[O:8])([CH3:28])[CH3:26]

Participants

3

Reactant 2

HCID 57486873Methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoateHCID 866305841,1-dimethylethyl[(3R,4S)-3-(methyloxy)-4-piperidinyl]carbamate

Product 1

HCID 57486907Methyl 3-[(3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(methyloxy)-1-piperidinyl]-2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]propanoateYield 142.8%

Procedure

The title compound was prepared according to the general method of Example 2(d) from 1,1-dimethylethyl[(3R,4S)-3-(methyloxy)-4-piperidinyl]carbamate (1.29 g, 5.63 mmol) and methyl 2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate (1.48 g, 5.63 mmol) to give the desired product (1.98 g, 71%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b9c00dc8d1a34343af3d8217341c83e0
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Reaction notes

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