Methanamine, N-methoxy-, hydrochloride (1:1) → Ethyl 4-(2-bromo-4-fluorophenyl)-6-(((S)-3-(methoxy(methyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524642Notes

Reaction equation

HRID 524642 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]=[C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)[NH:12][C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][C@H:22]2[C:27]([OH:29])=O)=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl.[CH3:36][NH:37][O:38][CH3:39]>>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[C:10]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:11]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][C@H:22]2[C:27](=[O:29])[N:37]([O:38][CH3:39])[CH3:36])[NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[N:14]1

Participants

3

Reactant 2

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 90044129(3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid

Product 1

HCID 73295973Ethyl 4-(2-bromo-4-fluorophenyl)-6-(((S)-3-(methoxy(methyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 35%

Procedure

(3S)-4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-3-carboxylic acid (4 g, 7.2 mmol) was reacted with N,O-dimethylhydroxylamine hydrochloride (0.84 g, 8.64 mmol) according to the procedure as described in Example 53 to give the title compound as a yellow solid (1.5 g, 35%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-e4c1d9b9ae0249d9b8f95848812f80b8
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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