Triphosgene → 1-Methoxy-3-(methoxymethoxy)benzene

HRID 527708Notes

Reaction equation

[CH2:1]([CH:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[NH2:22])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][O:4]1)[CH3:2].Cl[C:27](Cl)([O:29][C:30](=O)[O:31][C:32](Cl)(Cl)Cl)Cl>ClCCl>[CH2:1]([CH:3]1[C:7]2[C:8]([O:12][C:13]3[N:18]=[CH:17][C:16]([N:19]4[C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[NH:22][C:27]4=[O:29])=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][O:4]1)[CH3:2].[CH3:5][O:4][C:3]1[CH:7]=[CH:6][CH:11]=[C:32]([O:31][CH2:30][O:29][CH3:27])[CH:1]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a 50 mL round-bottomed flask N1-{6-[(3-ethyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-3-pyridinyl}-2-methylalaninamide (Intermediate 149, 17.2 mg, 0.050 mmol) was dissolved in Dichloromethane (3 mL) to give a pale yellow solution that was cooled at 0° C. TEA (0.035 mL, 0.252 mmol) was added followed by a dropwise addition of a solution of triphosgene (6.43 mg, 0.023 mmol) in dichloromethane (0.5 ml) and the reaction mixture was stirred at 0° C. for 20 minutes. The reaction mixture was evaporated in vacuo and the residue was purified by flash chromatography (Biotage system) on silica gel using a column SNAP 10 g and cyclohexane/ethyl acetate from 2:1 to 1:2 as eluents affording the title compound Example 45 (15.3 mg) as a white solid.

Workup

customto give a pale yellow solution that
customThe reaction mixture was evaporated in vacuo
customthe residue was purified by flash chromatography (Biotage system) on silica gel using a column SNAP 10 g and cyclohexane/ethyl acetate from 2:1 to 1:2 as eluents

Sources & evidence

ORD record: ord-f3a5987a4aac41a9a15da8417ba1d550
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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