Ethyl Acetate → HCID 69523377, compound

HRID 348453Notes

Reaction equation

HRID 348453 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:20])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH3:22][O:23][C:24]([C:26]1[N:27]([CH3:38])[C:28]2[C:33]([C:34]=1O)=[CH:32][C:31]([O:36][CH3:37])=[CH:30][CH:29]=2)=[O:25].C(OCC)(=O)C>CCCCCC>[CH3:22][O:23][C:24]([C:26]1[N:27]([CH3:38])[C:28]2[C:33]([C:34]=1[O:20][C:19](=[O:21])[CH2:18][O:17][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:16][N:15]=1)=[CH:32][C:31]([O:36][CH3:37])=[CH:30][CH:29]=2)=[O:25]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21087356[5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acidHCID 54685033HCID 54685033, compound

Product 1

HCID 69523377HCID 69523377, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

The titled compound was prepared from [5-(4-fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid using 3-hydroxy-5-methoxy-1-methyl-1H-indole-2-carboxylic acid methyl ester (40 mg, 0.17 mmol) as the source alcohol. Chromatography (1:1 ethyl acetate:hexane) through SiO2 yielded 13 mg (15%) of the titled compound. ESI-MS m/z 509 (MH+), 507 (M−H−).

Sources & evidence

ORD record
ord-c40ea1ecb44746a4bfbd1054093a4133
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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