HCID 178526779, compound → HCID 178508003, compound

HRID 711979Notes

Reaction equation

HRID 711979 reaction equation
[F:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([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)[CH2:5][CH2:4]1>[Pd].CO>[F:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10]2[C:15]([NH2:16])=[CH:14][N:13]=[C:12]3[CH:19]=[CH:20][S:21][C:11]=23)[CH2:7][CH2:8]1

Participants

4

Reactant 1

HCID 178526779HCID 178526779, compound

Product 1

HCID 178508003HCID 178508003, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-[trans-4-(fluoromethyl)cyclohexyl]-6-nitrothieno[3,2-b]pyridin-7-amine (0.20 g, 0.65 mmol) and 10% palladium on carbon (0.07 g) in methanol (7 mL) was hydrogenated under balloon pressure of H2 at room temperature for 1 h. The mixture was filtered. The filtrate was concentrated, diluted with dichloromethane, and then dried over MgSO4 and concentrated to give the desired product (0.11 g, 61%). LCMS calculated for C14H19FN3S (M+H)+: m/z=280.1. Found: 280.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with dichloromethane
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0243b3226a2c4fd78da8fd07a83f0635
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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