HCID 86717517, compound → HCID 86717519, compound

HRID 712059Notes

Reaction equation

HRID 712059 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][C@@H:7]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]3[CH:19]=[CH:20][S:21][C:11]=23)[CH2:6][CH2:5][C@@H:4]1[CH2:22][C:23]#[N:24]>[Pd].CO>[NH2:16][C:15]1[C:10]([NH:9][C@H:7]2[CH2:6][CH2:5][C@H:4]([CH2:22][C:23]#[N:24])[C@@H:3]([O:2][CH3:1])[CH2:8]2)=[C:11]2[S:21][CH:20]=[CH:19][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 1

HCID 86717517HCID 86717517, compound

Product 1

HCID 86717519HCID 86717519, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of {(1R,2S,4S)-2-methoxy-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}acetonitrile (racemic) (401 mg, 1.16 mmol) and 10% palladium on carbon (0.20 g) in methanol (7.7 mL) was subjected to balloon pressure of H2 at room temperature for 2 h. The mixture was filtered and the filtrate was concentrated and purified with flash chromatography (eluting with 15% methanol in dichloromethane) to give the desired product (342 mg, 93%). LCMS calculated for C16H21N4OS (M+H)+: m/z=317.1. Found: 317.1.

Workup

  1. customat room temperature
  2. customfor 2 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurified with flash chromatography (eluting with 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9b515ff6d0444e03844f6def69c6cbc8
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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