Sodium Bicarbonate → HCID 28485638, compound

HRID 1529563Notes

Reaction equation

HRID 1529563 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].Br[CH:6]1[C:11](=O)[CH2:10][CH2:9][N:8]([C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[CH2:7]1.C([O-])(O)=O.[Na+]>CCO>[F:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([N:8]1[CH2:9][CH2:10][C:11]2[N:1]=[C:2]([NH2:4])[S:3][C:6]=2[CH2:7]1)=[O:21]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 66608921HCID 66608921, compound

Product 1

HCID 28485638HCID 28485638, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Thiourea (0.84 g, 6.7 mmol) was added to a stirred suspension of 3-bromo-1-(2-fluorobenzoyl)-4-piperidinone (2.0 g, 6.7 mmol) and NaHCO3 (0.56 g, 6.7 mmol) in EtOH (50 mL). The mixture was stirred at 80° C. for 2 hours, cooled to room temperature and filtered. The filtrate was evaporated in vacuo to yield 5-(2-fluorobenzoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-amine (1.0 g, 54% yield) that was used in the next step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-53a4b5a706a44434840ef32e7bf4bb26
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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