Formic Acid → HCID 86598643, compound

HRID 500577Notes

Reaction equation

HRID 500577 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[CH3:11][O:12][C:13](=[O:34])[C:14]1[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[C:17]([NH2:23])=[C:16]([F:24])[C:15]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=1[F:33].C(OC(=O)C)=O>C1COCC1>[CH3:11][O:12][C:13](=[O:34])[C:14]1[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[C:17]([NH:23][CH:1]=[O:3])=[C:16]([F:24])[C:15]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][C:27]=1[F:33]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 75269Acetic-formic anhydrideHCID 86598641HCID 86598641, compound

Product 1

HCID 86598643HCID 86598643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To acetic anhydride (1.30 equiv.) is added formic acid (1.60 equiv.) at room temperature. The resulting mixture is stirred at 65 OC under N2 atmosphere for 2 hours, cooled to room temperature, and diluted with THF. To a solution of 5-acetyl-4-amino-2-(4-bromo-2-fluorophenylamino)-3-fluorobenzoic acid methyl ester (1.00 equiv.) in THF at 0° C. is added the above solution of acetic formic anhydride in THF. After stirring 30 minutes at 0° C., the reaction is quenched with MeOH. The reaction mixture is concentrated under reduced pressure to give the crude material that is purified by trituration or flash column chromatography to yield the desired product as necessary.

Workup

  1. stirringAfter stirring 30 minutes at 0° C.
  2. customthe reaction is quenched with MeOH
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customto give the crude material that
  5. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-396f12a997b54700bfea6826f3c8c1a2
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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