1,1'-Thiocarbonyldiimidazole → N-(5-(difluoromethoxy)thiazolo[5,4-b]pyridin-2-yl)-1H-imidazole-1-carbothioamide

HRID 250031Notes

Reaction equation

[F:1][CH:2]([F:14])[O:3][C:4]1[N:9]=[C:8]2[S:10][C:11]([NH2:13])=[N:12][C:7]2=[CH:6][CH:5]=1.[N:15]1([C:20](N2C=CN=C2)=[S:21])[CH:19]=[CH:18][N:17]=[CH:16]1>C(#N)C>[F:14][CH:2]([F:1])[O:3][C:4]1[N:9]=[C:8]2[S:10][C:11]([NH:13][C:20]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[S:21])=[N:12][C:7]2=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 70 °C

Procedure

5-(Difluoromethoxy)thiazolo[5,4-b]pyridin-2-amine (310 mg, 1.43 mmol) and di(1H-imidazol-1-yl)methanethione (311 mg, 1.75 mmol) were dissolved in acetonitrile (5 mL) and heated to 70° C. in a sealed vial for 10 hours. The vial was then stored in the freezer for 16 hours. The solids were collected by filtration and washed with acetonitrile to afford N-(5-(difluoromethoxy)thiazolo[5,4-b]pyridin-2-yl)-1H-imidazole-1-carbothioamide (296 mg, 0.72 mmol, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.77 (d, J=4.77 Hz, 1 H), 8.06 (d, J=8.53 Hz, 1 H), 8.01 (s, 1H), 7.72 (s, 1 H), 7.54 (s, 1 H), 6.94-7.13 (m, 1 H).

Workup

filtrationThe solids were collected by filtration
washwashed with acetonitrile

Sources & evidence

ORD record: ord-088004eca65348548ed53004079588fd
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863291B2

Reaction notes

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