4-(4-Bromophenyl)-4-hydroxypiperidine → 2-{2-[4-(4-Bromophenyl)-4-hydroxy-piperidin-1-yl]-2-oxo-ethoxy}-pyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348466Notes

Reaction equation

HRID 348466 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][C:19]([OH:21])=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2([OH:35])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[N:15][C:14]([O:17][CH2:18][C:19]([N:32]3[CH2:31][CH2:30][C:29]([C:26]4[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][CH:25]=4)([OH:35])[CH2:34][CH2:33]3)=[O:21])=[N:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 939114-(4-Bromophenyl)-4-hydroxypiperidineHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 867603862-{2-[4-(4-Bromophenyl)-4-hydroxy-piperidin-1-yl]-2-oxo-ethoxy}-pyrimidine-5-carboxylic acid (4-fluorophenyl)amideYield 84%

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 4-(4-bromophenyl)-piperidin-4-ol (56 mg, 0.22 mmol) as the coupling partner. Concentration (no chromatography) yielded 76 mg (84%) of the titled compound. ESI-MS m/z 530, 532 (MH+), 527, 529 (M−H−).

Workup

  1. concentrationConcentration (no chromatography)

Sources & evidence

ORD record
ord-eec8ff0fa6ee4dda9a96b46d4f5577c6
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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