Sodium Carbonate → HCID 23568733, compound

HRID 1822795Notes

Reaction equation

[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:25])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[N:18]=[C:17](Cl)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2].[F:26][C:27]([F:39])([F:38])[O:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:25])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH3:23])[N:18]=[C:17]([C:32]2[CH:31]=[CH:30][C:29]([O:28][C:27]([F:26])([F:38])[F:39])=[CH:34][CH:33]=2)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(2-chloro-6-propyl-pyrimidin-4-ylamino)-4-methyl-pentanoic acid (3-ethoxy-propyl)-amide (31.4 mg), 4-(trifluoromethoxy)phenylboronic acid (19 mg), sodium carbonate (0.4M aqueous solution, 0.5 mL), and acetonitrile (0.5 mL) was degassed with argon for five minutes. Tetrakis(triphenylphosphine) palladium(0) was added and the mixture was heated to 80° C. for 4 hours. The reaction mixture was taken up in ethyl acetate, washed twice with brine, and the volatiles were removed in vacuo. The product was purified on silica gel, using 50% ethyl acetate/hexanes as the mobile phase, to give 13.5 mg of 4-methyl-2-[6-propyl-2-(4-trifluoromethoxyphenyl)pyrimidin-4-ylamino] pentanoic acid (3-ethoxypropyl) amide. ESI-MS (m/z) 497 [M+H]+.

Workup

customwas degassed with argon for five minutes
additionTetrakis(triphenylphosphine) palladium(0) was added
washwashed twice with brine
customthe volatiles were removed in vacuo
customThe product was purified on silica gel

Sources & evidence

ORD record: ord-48c2993ef4014602bbc862b50b6a79d2
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037916B2

Reaction notes

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