Methylamine → HCID 68490661, compound

HRID 1878024Notes

Reaction equation

HRID 1878024 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][CH2:9][C:10]2([C:24]([F:27])([F:26])[F:25])[C:15]3[CH:16]=[C:17]([C:20]([OH:22])=O)[CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:23])[O:11]2)=[O:7])=[CH:4][CH:3]=1.C1N=C[N:32](C(N2C=NC=C2)=O)[CH:31]=1.CN>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][C:10]2([C:24]([F:26])([F:25])[F:27])[C:15]3[CH:16]=[C:17]([C:20]([NH:32][CH3:31])=[O:22])[CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:23])[O:11]2)=[O:7])=[CH:28][CH:29]=1

Participants

7

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 68486396HCID 68486396, compound

Product 1

HCID 68490661HCID 68490661, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{[(4-Fluorobenzoyl)amino]methyl}-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazine-6-carboxylic acid (30 mg, 0.073 mmol) and CDI (23.6 mg, 0.15 mmol) were dissolved in THF (230 μL) and DMF (90 μL), and the solution was stirred at room temperature for 30 minutes and thereafter, methylamine (182 μL, 0.36 mmol) was added thereto. The reaction solution was stirred at room temperature for 30 minutes and then diluted with ethyl acetate, which was washed sequentially with water and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography, whereby the objective compound (10.2 mg, 33%) was obtained as a white solid.

Workup

  1. washwas washed sequentially with water and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customAfter the drying agent was removed by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography, whereby the objective compound (10.2 mg, 33%)
  6. customwas obtained as a white solid

Sources & evidence

ORD record
ord-a8a52e79c433407fbda76272eeb0b9cd
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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