Acetic Anhydride → HCID 59140138, compound

HRID 2076179Notes

Reaction equation

HRID 2076179 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH2:12])=[N:6][C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][C:15]=1[F:24].[C:26](OC(=O)C)(=[O:28])C>C(O)=O>[CH3:1][O:2][C:3](=[O:25])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH:12][CH:26]=[O:28])=[N:6][C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([Si:20]([CH3:21])([CH3:23])[CH3:22])=[CH:16][C:15]=1[F:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 591401506-Aminomethyl-5-fluoro-2-(2-fluoro-4-trimethylsilanyl-phenylamino)-nicotinic acid methyl ester

Product 1

HCID 59140138HCID 59140138, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a solution of 6-aminomethyl-5-fluoro-2-(2-fluoro-4-trimethylsilanyl-phenylamino)-nicotinic acid methyl ester (2.0 g, 5.5 mmol) in formic acid (30 mL) at 0° C. was added acetic anhydride (6 mL). The reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was concentrated in vacuo and the resultant residue azeotroped with toluene, then dissolved in dichloromethane. This organic layer was washed with a saturated aqueous solution of sodium bicarbonate, followed by brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a dark brown solid (2.1 g, 100%). LCMS (method B): RT=4.36 min, [M+H]+=394.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resultant residue azeotroped with toluene
  3. dissolutiondissolved in dichloromethane
  4. washThis organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c5ac4f8026ec4faa9261b32fb05c0c01
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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