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

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

Participants

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

filtrationthe crude product collected by filtration
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

Linked notes

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