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

HRID 1884165Notes

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-5e587198d6954762b0a425e8a939a461
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06762320B2

Reaction notes

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