Glycine ethyl ester, hydrochloride → Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-ethoxy-2-oxoethyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylate

HRID 524656Notes

Reaction equation

HRID 524656 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][CH:23]([C:27](O)=[O:28])[CH2:22]2)=[C:10]1[C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl.[NH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O: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][CH:23]([C:27](=[O:28])[NH:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:22]2)[NH:12][C:13]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[N:14]1

Participants

3

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 732961284-((6-(2-Bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid

Product 1

HCID 118107586Ethyl 4-(2-bromo-4-fluorophenyl)-6-((2-((2-ethoxy-2-oxoethyl)carbamoyl)morpholino)methyl)-2-(thiazol-2-yl)-1,4-dihydropyrimidine-5-carboxylateYield 82.1%

Procedure

4-((6-(2-bromo-4-fluorophenyl)-5-(ethoxycarbonyl)-2-(thiazol-2-yl)-3,6-dihydropyrimidin-4-yl)methyl)morpholine-2-carboxylic acid (0.8 g, 1.45 mmol) was reacted with ethyl 2-aminoacetate hydrochloride (0.31 g, 2.17 mmol) according to the procedure as described in Example 53 to give the title compound as a yellow solid (0.76 g, 82%). The compound was characterized by the following spectroscopic data:

Sources & evidence

ORD record
ord-09916f527dc14ade9c39eb740770b31e
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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