Ammonia → HCID 178493435, compound

HRID 56466Notes

Reaction equation

O1CCO[CH:2]1[C:6]1[C:7]([NH2:23])=[CH:8][C:9]([F:22])=[C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[CH:13]=2)[CH:11]=1.C([N:26]([CH2:29]C)CC)C.ClC(Cl)([O:34]C(=O)OC(Cl)(Cl)Cl)Cl.N.CO.Cl>C1COCC1.O1CCOCC1>[CH3:19][O:18][C:16]1[CH:17]=[C:12]([C:10]2[CH:11]=[C:6]3[C:7](=[CH:8][C:9]=2[F:22])[N:23]=[C:29]([OH:34])[N:26]=[CH:2]3)[CH:13]=[C:14]([O:20][CH3:21])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(1,3-dioxolan-2-yl)-2-fluoro-3′,5′-dimethoxybiphenyl-4-amine (1.9 g, 6.0 mmol) and triethylamine (3.0 mL, 21.4 mmol) in THF (20 mL) at 0° C. was added triphosgene (0.6 g, 2.0 mmol), and stirred at 0° C. for 0.5 hour. After that, ammonia in methanol (3 mL, 21 mmol, 7 mol/L) was added. The reaction was stirred at 0° C. for 30 mins and quickly warmed to ambient temperature. After stirred for additional 30 mins at room temperature, the reaction mixture was acidified with 4 mol/L HCl in dioxane (8.2 mL) to pH 2 and then stirred at room temperature for 1 hour. Then the resultant solution was concentrated and purified by silica gel column chromatography (dichloromethane/methanol=50/1 to 10/1) to afford the title compound (2.0 g, 99%) as a yellow solid. MS (ES+) C16H13FN2O3 requires: 300, found: 301 [M+H]+.

Workup

stirringThe reaction was stirred at 0° C. for 30 mins
temperaturequickly warmed to ambient temperature
stirringAfter stirred for additional 30 mins at room temperature
stirringstirred at room temperature for 1 hour
concentrationThen the resultant solution was concentrated
custompurified by silica gel column chromatography (dichloromethane/methanol=50/1 to 10/1)

Sources & evidence

ORD record: ord-1eb01e1e19c440abb32c53a2b4e36edb
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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