Thiourea → tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylate

HRID 1402666Notes

Reaction equation

HRID 1402666 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH:10](Br)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]([NH2:19])=[S:18]>C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:16]=[C:17]([NH2:19])[S:18][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 106839701-tert-Butyloxycarbonyl-3-bromo-4-oxopiperidine

Product 1

HCID 11357283tert-butyl 2-amino-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridine-5-carboxylateYield 111.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 3-Bromo-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (10 grams, 35 mmol, obtained in above step) and thiourea (3.28 grams, 42 mmol) in isopropanol (100 mL) was refluxed for 1 hour. After completion of reaction, reaction mass was concentrated and resulted crude was triturated with diethyl ether (50 mL), solids were filtered and dried under vacuum to obtain the title compound (10 grams).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customAfter completion of reaction, reaction mass
  3. concentrationwas concentrated
  4. customresulted crude
  5. customwas triturated with diethyl ether (50 mL), solids
  6. filtrationwere filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ceaa360decc84bf8a6c6d736307d990c
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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