HCID 66699712, compound → HCID 24985020, compound

HRID 388127Notes

Reaction equation

HRID 388127 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-6de64f05b03e411f8ba72028bab6a53f
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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