Triethylamine → {4-[4-(Benzyloxycarbonylamino)-2-fluorophenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

HRID 2066180Notes

Reaction equation

HRID 2066180 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.C(N([CH2:32][CH3:33])CC)C.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36].[C:44](=[O:47])([O-])[OH:45].[Na+]>O1CCCC1.C(OCC)(=O)C>[C:38]1([O:37][C:35](=[O:36])[N:24]([C:20]2[CH:19]=[C:18]([O:17][C:14]3[CH:15]=[CH:16][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:26])=[CH:12][C:13]=3[F:25])[CH:23]=[CH:22][N:21]=2)[C:44]([O:45][C:33]2[CH:32]=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:47])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 57677357[4-(2-Aminopyridin-4-yloxy)-3-fluorophenyl]carbamic acid benzyl ester

Product 1

HCID 59597005{4-[4-(Benzyloxycarbonylamino)-2-fluorophenoxy]pyridin-2-yl}-N-(phenoxycarbonyl)carbamic acid phenyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [4-(2-aminopyridin-4-yloxy)-3-fluorophenyl]carbamic acid benzyl ester (1.0 g) in tetrahydrofuran (25 ml) were added triethylamine (0.983 ml) and phenyl chloroformate (0.884 ml) in this order while stirring in an ice water bath. The reaction mixture was stirred at room temperature for 30 min. After the reaction mixture was diluted with ethyl acetate, a saturated aqueous solution of sodium hydrogencarbonate was added thereto, and the reaction mixture was stirred. The organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was dried under reduced pressure to provide a crude product of the titled compound as a brown oil (1.945 g).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 min
  2. stirringthe reaction mixture was stirred
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and brine in this order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-ca65087d91a74cc4b71771422d5b1cc2
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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