1-Propanol → HCID 59856773, compound

HRID 1174746Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][C:23]3[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=3[F:30])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH2:31]([OH:34])[CH2:32][CH3:33].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.[Cu](I)I>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([O:34][CH2:31][CH2:32][CH3:33])=[CH:25][C:24]=3[F:30])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-[5-cyano-6-(2-fluoro-4-iodo-phenylamino)-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (250 mg, 0.48 mmol), propan-1-ol (2 mL, excess), copper iodide (9.1 mg, 0.048 mmol), 1,10-phenanthroline (18.1 mg, 0.096 mmol) and cesium carbonate (313 mg, 0.96 mmol) in dioxane (3.5 mL) was heated under microwave irradiation for 30 min at 90° C. The crude mixture was concentrated in vacuo and purified by HPLC to provide compound A65 as a white solid (10 mg, 12%). Exact mass calculated for C23H28FN5O4 457.50, found 458.8 (MH+).

Workup

concentrationThe crude mixture was concentrated in vacuo
custompurified by HPLC

Sources & evidence

ORD record: ord-a0d18d34e45d4df4ac5e6746b0ead59a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838525B2

Reaction notes

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