Formic Acid → N-[2-Fluoro-4-(4-fluoro-benzyloxy)-phenyl]-2-formylamino-acetamide

HRID 1827441Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:18][C:17]=1[F:31])=[O:14].Cl>C(Cl)Cl.[Na].[H][H]>[F:31][C:17]1[CH:18]=[C:19]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH:20]=[CH:21][C:16]=1[NH:15][C:13](=[O:14])[CH2:12][NH:11][CH:1]=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of acetic anhydride (40 mg, 0.39 mmol) and formic acid (22 mg, 0.48 mmol) was stirred at 0° C. and then heated uat 60° C. for 1 h. Step 2: During this time, 2-amino-N-[2-fluoro-4-(4-fluoro-benzyloxy)-phenyl]-acetamide (1:1) hydrochloride (50 mg, 0.15 mmol) was extracted with DCM and sodium hydrogen carboante (saturated) and the organic layer evaporated. Then to a mixture of the acetic formic anhydride (Step 1) in dry THF (0.5 mL) was added a solution of the amine (Step 2) in dry THF (1 mL) at room temperature and the resulting mixture stirred for 10 min. Then the reaction mixture was evaporated leave the title compound (44.1 mg, 91%) as a white solid. MS: m/e=321.1 (M++H).

Workup

temperatureheated uat 60° C. for 1 h
customthe organic layer evaporated
additionThen to a mixture of the acetic formic anhydride (Step 1) in dry THF (0.5 mL)
additionwas added a solution of the amine (Step 2) in dry THF (1 mL) at room temperature
stirringthe resulting mixture stirred for 10 min
customThen the reaction mixture was evaporated

Sources & evidence

ORD record: ord-b74e85e3a9fc467184f8d856fdd00454
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053245B2

Reaction notes

Loading…