HCID 66699712, compound → HCID 24985020, compound

HRID 1014723Notes

Reaction equation

HRID 1014723 reaction equation
[NH2:1][C:2]1[C:3]([NH:19][C@@H:20]([CH:23]([CH3:25])[CH3:24])[CH2:21][OH:22])=[N:4][C:5]([C:8]2[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[O:17][CH3:18])=[CH:6][CH:7]=1.C(C1C=CC(OC)=C(C2N=C(N[C@@H](C(C)C)[CH2:43][OH:44])C([N+]([O-])=O)=CC=2)C=1)(C)C>C(O)C.[Pd]>[OH:22][CH2:21][C@@H:20]([N:19]1[C:3]2=[N:4][C:5]([C:8]3[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=3[O:17][CH3:18])=[CH:6][CH:7]=[C:2]2[NH:1][C:43]1=[O:44])[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 66699712HCID 66699712, compoundHCID 66700005HCID 66700005, compound

Product 1

HCID 24985020HCID 24985020, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-2-(3-Amino-6-(5-isopropyl-2-methoxyphenyl)pyridin-2-ylamino)-3-methylbutan-1-ol. A solution of (S)-2-(6-(5-isopropyl-2-methoxyphenyl)-3-nitropyridin-2-ylamino)-3-methylbutan-1-ol (0.33 g, 0.88 mmol) in ethanol (30 mL) was purged with nitrogen for several min. Following addition of palladium on carbon (0.038 g, 0.35 mmol), the flask was evacuated and a hydrogen filled balloon was placed on the reaction. After stirring at room temperature for 18 h, the reaction was filtered and the solvent removed under reduced pressure to afford the title compound (0.30 g, 99% yield). MS (ESI) m/z 344.3 [M+1]+.

Workup

  1. customthe flask was evacuated
  2. customa hydrogen filled balloon was placed on the reaction
  3. filtrationthe reaction was filtered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-96128a903f0b4b6cb56a6ce102348989
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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