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Water → N-(5-(pyrazin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)acetamide

HRID 39362
Notes
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Reaction equation

HRID 39362 reaction equation
[N:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[S:3][C:2]=1[NH:10][C:11](=[O:13])[CH3:12].Cl[C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1.O>CN1C(=O)CCC1>[N:16]1[CH:17]=[CH:18][N:19]=[CH:20][C:15]=1[N:6]1[CH2:7][CH2:8][C:9]2[N:1]=[C:2]([NH:10][C:11](=[O:13])[CH3:12])[S:3][C:4]=2[CH2:5]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 73277ChloropyrazineHCID 28274565N-(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)acetamide

Product 1

HCID 46873663N-(5-(pyrazin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)acetamideYield 9.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

As shown in step 10-iv of Scheme 10, to a solution of 50 mg of Compound 1035 in 3 mL of NMP was added 100 mg of 2-chloro pyrazine. The reaction mixture was warmed to 250° C. for 10 minutes under microwave irradiation. The reaction was poured into water (10 mL) and the crude product collected by filtration. The crude solid was purified by silica gel chromatography (CH2Cl2 to EtOH) to provide N-(5-(pyrazin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)acetamide (Compound 1, 6.8 mg): ESMS (M+H) 276.16.

Workup

  1. filtrationthe crude product collected by filtration
  2. customThe crude solid was purified by silica gel chromatography (CH2Cl2 to EtOH)

Sources & evidence

ORD record
ord-33e117da437743818d6eadef14513599
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524906B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes