HCID 71075495, compound → HCID 77231057, compound

HRID 1028110Notes

Reaction equation

HRID 1028110 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:14][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)=[N:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[S:14][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:17][CH2:16]3)=[N:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 71075495HCID 71075495, compound

Product 1

HCID 77231057HCID 77231057, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 1-[5-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate (75 mg, 0.21 mmol) in ethyl acetate (1.9 mL) and acetic acid (0.19 mL) was added 10% palladium on carbon (22 mg, 0.021 mmol), and the mixture was stirred under an atmosphere of hydrogen (balloon) for 3 hours. The mixture was filtered through celite, washing with ethyl acetate and the filtrate concentrated under reduced pressure. Purification by CombiFlash (30-70% ethyl acetate:hexanes) provided 60 mg (0.18 mmol, 87% yield) of ethyl 1-[5-(3-aminophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashing with ethyl acetate
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customPurification by CombiFlash (30-70% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-bd2853cbbef84ff7a609abc9c174f109
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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