Tert-butyl 3-fluoro-4-[(6-nitrothieno[3,2-b]pyridin-7-yl) amino]piperidine-1-carboxylate → tert-Butyl 4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]-3-fluoropiperidine-1-carboxylate

HRID 711968Notes

Reaction equation

HRID 711968 reaction equation
[F:1][CH:2]1[CH:7]([NH:8][C:9]2[C:14]([N+:15]([O-])=O)=[CH:13][N:12]=[C:11]3[CH:18]=[CH:19][S:20][C:10]=23)[CH2:6][CH2:5][N:4]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:3]1>[Pd].CO>[NH2:15][C:14]1[C:9]([NH:8][CH:7]2[CH2:6][CH2:5][N:4]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:3][CH:2]2[F:1])=[C:10]2[S:20][CH:19]=[CH:18][C:11]2=[N:12][CH:13]=1

Participants

4

Reactant 1

HCID 86717437Tert-butyl 3-fluoro-4-[(6-nitrothieno[3,2-b]pyridin-7-yl) amino]piperidine-1-carboxylate

Product 1

HCID 86717436tert-Butyl 4-[(6-aminothieno[3,2-b]pyridin-7-yl)amino]-3-fluoropiperidine-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 3-fluoro-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]piperidine-1-carboxylate (0.32 g, 0.81 mmol) and 10% palladium on carbon (80 mg) in methanol (8 mL) was hydrogenated under balloon pressure of H2 at room temperature for 5 h. The reaction mixture was filtered, and the filtrate was concentrated to give the desired product (0.23 g, 78%) as a mixture of cis- and trans-isomers mixture. LCMS calculated for C17H24FN4O2S (M+H)+: m/z=367.2. Found: 367.1.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f772b47a4cc441a5944bb0542b6be7b7
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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