Water → HCID 86732474, compound

HRID 1776446Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:29]=[C:28]([F:30])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=3)[C:11]([C:19]3[N:24]=[C:23]([NH2:25])[C:22]([O:26][CH3:27])=[CH:21][N:20]=3)=[N:10]2)=[C:6]([F:31])[CH:5]=1)[CH3:2].Cl.F[C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1.[H-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([F:31])[C:7]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=3)[C:11]([C:19]3[N:24]=[C:23]([NH:25][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)[C:22]([O:26][CH3:27])=[CH:21][N:20]=3)=[N:10]2)=[C:28]([F:30])[CH:29]=1)[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

100 mg of 2-[1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-indazol-3-yl]-5-methoxypyrimidin-4-amine (1-4-6, 0.236 mmol, 1.0 eq.) and 94.2 mg 4-Fluoropyridin hydrochloride (0.705 mmol, 3.0 eq.) were dissolved in 1.1 ml of dry N,N-dimethylformamide. 113 mg sodium hydride (60%, 2.82 mmol, 12 eq.) were added. The reaction mixture was stirred at 90° C. for 2 h. Water and ethyl acetate were added and the aqueous layer was washed with ethyl acetate twice. The combined organic layers were dried over a silicone filter and concentrated in vacuum. The residue was purified by HPLC to yield 46 mg (0.09 mmol, 38%) of the analytically pure target compound.

Workup

washthe aqueous layer was washed with ethyl acetate twice
dry with materialThe combined organic layers were dried over a silicone
filtrationfilter
concentrationconcentrated in vacuum
customThe residue was purified by HPLC
customto yield 46 mg (0.09 mmol, 38%) of the analytically pure target compound

Sources & evidence

ORD record: ord-e3b44ba6d60b44c5aff56da557e4a64d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265763B2

Reaction notes

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