Exo-2-bornanamine → 2-(Bicyclo[2.2.1]hept-2-ylcarbamoylmethoxy)pyrimidine-5-carboxylic acid (4-fluorophenyl)amide

HRID 348481Notes

Reaction equation

HRID 348481 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.[NH2:22][CH:23]1[CH2:28][CH:27]2[CH2:29][CH:24]1[CH2:25][CH2:26]2>>[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](=[O:21])[NH:22][CH:23]3[CH2:28][CH:27]4[CH2:29][CH:24]3[CH2:25][CH2:26]4)=[N:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 98480Exo-2-bornanamineHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid

Product 1

HCID 867603932-(Bicyclo[2.2.1]hept-2-ylcarbamoylmethoxy)pyrimidine-5-carboxylic acid (4-fluorophenyl)amideYield 71%

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 2-aminonorbornane (21 μL, 0.18 mmol) as the coupling partner. Concentration (no chromatography) yielded 38 mg (71%) of the titled compound. ESI-MS m/z 385 (MH+), 383 (M−H−).

Workup

  1. concentrationConcentration (no chromatography)

Sources & evidence

ORD record
ord-97e94e58c2894e498fbf331a634b5b11
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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