Tetrahydrofuran → HCID 86683843, compound

HRID 340430Notes

Reaction equation

HRID 340430 reaction equation
O1CCCC1.C([NH:13][C:14]1[N:19]=[C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:17]([F:35])=[CH:16][C:15]=1[C:36]([NH:38][C:39]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:41])[CH3:40])=[O:37])C1C=CC=CC=1.[H][H]>[OH-].[Pd+2].[OH-].CO>[NH2:13][C:14]1[N:19]=[C:18]([NH:20][C@H:21]2[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]2[NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:31])[CH3:32])[C:17]([F:35])=[CH:16][C:15]=1[C:36]([NH:38][C:39]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)([CH3:40])[CH3:41])=[O:37]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 86683844HCID 86683844, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86683843HCID 86683843, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Palladium hydroxide (0.29 g) was added to a solution of tetrahydrofuran (7.2 ml) and methanol (14.3 ml) containing tert-butyl cis-2-(6-benzylamino-3-fluoro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (1.43 g), followed by stirring at room temperature for 1 hour in a hydrogen atmosphere. Insoluble matter was removed by filtration, and filter cake was washed with ethyl acetate. The filtrate was mixed with the washing solution, and the solvent was distilled away under reduced pressure. Diisopropylether and hexane were added to the obtained residue, solid matter was collected by filtration, and a white solid of tert-butyl cis-2-(6-amino-3-fluoro-5-(2-phenylpropan-2-ylaminocarbonyl)pyridin-2-ylamino)cyclohexylcarbamate (870 mg) was thus obtained.

Workup

  1. customInsoluble matter was removed by filtration
  2. filtrationfilter cake
  3. washwas washed with ethyl acetate
  4. additionThe filtrate was mixed with the washing solution
  5. distillationthe solvent was distilled away under reduced pressure
  6. additionDiisopropylether and hexane were added to the obtained residue, solid matter
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-70f192df5cf345609ac40b6b71ab8357
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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