Triethylamine → HCID 57677472, compound

HRID 492840Notes

Reaction equation

HRID 492840 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=2)=[C:13]([F:25])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.ClC([O:37][C:38]1C=CC=CC=1)=O.[CH3:44][NH:45][CH:46]1CCN(C)CC1>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:26])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:38]([N:45]([CH3:46])[CH:44]3[CH2:33][CH2:32][N:29]([CH3:27])[CH2:30][CH2:31]3)=[O:37])[CH:19]=2)=[C:13]([F:25])[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 5663231-Methyl-4-(methylamino)piperidineHCID 57677357[4-(2-Aminopyridin-4-yloxy)-3-fluorophenyl]carbamic acid benzyl ester

Product 1

HCID 57677472HCID 57677472, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving [4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]carbamic acid benzyl ester (41 mg) in N,N-dimethylformamide (2 ml) under a nitrogen atmosphere, triethylamine (0.0485 ml) and phenyl chloroformate (0.0545 ml) were added while stirring in an ice water bath. The reaction mixture was brought to room temperature and the mixture was stirred for 30 minutes. Methyl-(1-methylpiperidin-4-yl)amine (0.0675 ml) was added to the reaction mixture and stirred therewith for 20 hours. The reaction mixture was partitioned between ethyl acetate (30 ml) and saturated aqueous ammonium chloride (20 ml). The separated organic layer was washed with saturated aqueous ammonium chloride (20 ml), water (20 ml) and brine (20 ml) and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and then the resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=2:3 to 1:5). Fractions containing the target compound were concentrated under reduced pressure to provide the title compound (38.7 mg, 65.7%) as a colorless oil. ESI-MS (neg.) (m/z): 506[M−H]−.

Workup

  1. customwas brought to room temperature
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringstirred
  4. customThe reaction mixture was partitioned between ethyl acetate (30 ml) and saturated aqueous ammonium chloride (20 ml)
  5. washThe separated organic layer was washed with saturated aqueous ammonium chloride (20 ml), water (20 ml) and brine (20 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe resultant residue was purified by silica gel column chromatography (Fuji Silysia NH, eluent; heptane:ethyl acetate=2:3 to 1:5)
  9. additionFractions containing the target compound
  10. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-b38a7b14e4f44edd82596ddbc19c7ae5
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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