HCID 71529464, compound → HCID 71273879, compound

HRID 1752479Notes

Reaction equation

HRID 1752479 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C:5]([F:32])([F:31])[C@:6]([C:9]2[N:14]=[C:13]([NH:15][C:16]([C:18]3[C:23]([NH2:24])=[N:22][C:21]([C:25]([F:28])([F:27])[CH3:26])=[C:20](Cl)[N:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[F:30])([CH3:8])[N:7]=1>CO.C1COCC1.[Pd]>[NH2:1][C:2]1[O:3][CH2:4][C:5]([F:31])([F:32])[C@:6]([C:9]2[N:14]=[C:13]([NH:15][C:16]([C:18]3[C:23]([NH2:24])=[N:22][C:21]([C:25]([F:28])([F:27])[CH3:26])=[CH:20][N:19]=3)=[O:17])[CH:12]=[CH:11][C:10]=2[F:30])([CH3:8])[N:7]=1

Participants

4

Reactant 1

HCID 71529464HCID 71529464, compound

Product 1

HCID 71273879HCID 71273879, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3-amino-6-chloro-5-(1,1-difluoro-ethyl)-pyrazine-2-carboxylic acid [6-((R)-2-amino-5,5-difluoro-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-5-fluoro-pyridin-2-yl]-amide [Example 34] (54 mg, 0.113 mmol) in MeOH/THF (1:1, 10 ml) was added Pd/C 10% (BASF 4505 D/R E, 12 mg) and the mixture was set under an hydrogen atmosphere. After 2.5 h more Pd/C 10% (BASF 4505 D/R E, 11 mg) was added and the hydrogenation continued for another 2.5 h. The reaction mixture was filtered through a pad of Celite, washed with MeOH and the solvent evaporated. The residue was purified by chromatography on silica gel (DCM to DCM/MeOH 9:1) to provide the title compound as yellow foam.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washwashed with MeOH
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography on silica gel (DCM to DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-003f555c80774047af6fd8f5d1b9d770
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

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