Methanol → HCID 24788497, compound

HRID 1712686Notes

Reaction equation

HRID 1712686 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][C@@H:20]([OH:23])[CH2:19]3)=[O:17])[CH:10]=2)[C:5]([F:24])=[CH:4][C:3]=1[NH:25][C:26]([C:28]1([C:31]([O:33]CC2C=CC=CC=2)=[O:32])[CH2:30][CH2:29]1)=[O:27].CO.[H][H].[CH2:45]([N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])[CH3:46]>O1CCCC1.[Pd]>[CH2:45]([N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])[CH3:46].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:22][CH2:21][C@@H:20]([OH:23])[CH2:19]3)=[O:17])[CH:10]=2)[C:5]([F:24])=[CH:4][C:3]=1[NH:25][C:26]([C:28]1([C:31]([OH:33])=[O:32])[CH2:29][CH2:30]1)=[O:27]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 24788500HCID 24788500, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24788497HCID 24788497, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 1-[({2,5-difluoro-4-[(2-{[((R)-3-hydroxypyrrolidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}amino)carbonyl]cyclopropanecarboxylate (156.8 mg) was dissolved in tetrahydrofuran and methanol (2:1) (6 ml) under a nitrogen atmosphere. 10% palladium on carbon (68.6 mg) was added, and the air in the reaction vessel was replaced by hydrogen, and the mixture was stirred at room temperature for 16 hours and 30 minutes. The air in the reaction vessel was replaced by nitrogen, and triethylamine (0.112 ml) was added, and the mixture was stirred for 30 minutes. The catalyst was removed by filtration, and washed with methanol. The filtrate was concentrated under reduced pressure to give the title compound (185.3 mg, quant.) as a white solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe catalyst was removed by filtration
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce03e23df5a34aee97e6f2c13884928d
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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