(4R)-4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid → (4R)-4-(3,4-Difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid {3-[4-(4-fluorophenyl)-4-hydroxy-piperidin-1-yl]-propyl}-amide

HRID 1250708Notes

Reaction equation

HRID 1250708 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)([OH:13])[CH2:9][CH2:8]1.[F:21][C:22]1[CH:23]=[C:24]([C@@H:29]2[C:34]([C:35](O)=[O:36])=[C:33]([CH3:38])[NH:32][C:31](=[O:39])[NH:30]2)[CH:25]=[CH:26][C:27]=1[F:28].FC1C=C([C@@H]2C(C(O)=O)=C(COC)NC(=O)N2)C=CC=1F>>[F:20][C:17]1[CH:16]=[CH:15][C:14]([C:10]2([OH:13])[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][CH2:4][NH:3][C:35]([C:34]3[C@@H:29]([C:24]4[CH:25]=[CH:26][C:27]([F:28])=[C:22]([F:21])[CH:23]=4)[NH:30][C:31](=[O:39])[NH:32][C:33]=3[CH3:38])=[O:36])[CH2:12][CH2:11]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 10587936(4R)-4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acidHCID 10780384(4R)-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylic acidHCID 183266201-(3-Amino-propyl)-4-(4-fluorophenyl)-piperidine-4-ol dihydrochloride

Product 1

HCID 59870645(4R)-4-(3,4-Difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid {3-[4-(4-fluorophenyl)-4-hydroxy-piperidin-1-yl]-propyl}-amide

Procedure

1-(3-Amino-propyl)-4-(4-fluorophenyl)-piperidine-4-ol dihydrochloride was used in place of 2-(1-(3-Amino-propyl)-piperidine-4-yl]-5-fluoro-benzonitrile dihydrochloride and (4R)-4-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid was used go in place of (4R)-4-(3,4-difluorophenyl)-6-methoxymethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid.

Sources & evidence

ORD record
ord-8d619f1a21504804b615d628fc633518
Source dataset
uspto-grants-2002_01
Patent number
US06339090B1

Reaction notes

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