5-Bromopyrimidine-2-carboxylic acid → HCID 71252096, compound
Reaction equation
Cl.[CH3:2][C:3]1[C:4]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.[Br:16][C:17]1[CH:18]=[N:19][C:20]([C:23](O)=[O:24])=[N:21][CH:22]=1>>[Br:16][C:17]1[CH:18]=[N:19][C:20]([C:23]([N:13]2[CH2:12][CH2:11][N:10]([C:4]3[C:3]([CH3:2])=[CH:8][C:7]([CH3:9])=[CH:6][N:5]=3)[CH2:15][CH2:14]2)=[O:24])=[N:21][CH:22]=1Participants
Procedure
Using 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (528 mg) described in Preparation Example 80 and 5-bromopyrimidine-2-carboxylic acid (406 mg) and by the reaction and treatment in the same manner as in Example 97, (5-bromopyrimidin-2-yl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone (750 mg) was obtained. Using this compound (750 mg) and (R)-4-methyl-2-oxazolidinone (303 mg) and by the reaction and treatment in the same manner as in Example 1, (R)-3-[2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]pyrimidin-5-yl]-4-methyloxazolidin-2-one was obtained. The obtained (R)-3-[2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]pyrimidin-5-yl]-4-methyloxazolidin-2-one was dissolved in ethyl acetate, 4N hydrogen chloride/ethyl acetate (0.4 mL) was added, and the precipitate was collected by filtration to give the title compound (509 mg).
Sources & evidence
- ORD record
- ord-0507763d52a94669bd3e4b91262d0b41
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08816079B2
Reaction notes
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