1,1'-Thiocarbonyldiimidazole → HCID 123678754, compound

HRID 716189Notes

Reaction equation

[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[S:2].N[C:14]1C=NC=C[C:19]=1[C:20]1[CH:21]=[C:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:23]=[C:24]([CH3:26])[CH:25]=1>C1COCC1.CCOC(C)=O>[N:8]([C:12]1[CH:11]=[N:10][CH:9]=[CH:14][C:19]=1[C:20]1[CH:21]=[C:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[CH:23]=[C:24]([CH3:26])[CH:25]=1)=[C:1]=[S:2]

Participants

Conditions

Temperature: 60 °C

Procedure

tert-butyl (3-(3-isothiocyanatopyridin-4-yl)-5-methylphenyl) carbamate. 1,1′-thiocarbonyldiimidazole (155 mg, 0.78 mmol, Sigma-Aldrich) was added to a solution of tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl)carbamate (117 mg, 0.39 mmol) in THF (4 mL) at RT. The reaction mixture was heated at 60° C. for 2 h. The mixture was cooled to RT, diluted with EtOAc, washed with water and the organic layer was dried over anh. Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes) to provide tert-butyl (3-(3-isothiocyanatopyridin-4-yl)-5-methylphenyl)carbamate (63 mg, 0.19 mmol, 47% yield) as a white solid. MS (ESI, pos. ion) m/z: 342.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.58 (s, 1 H), 8.49 (d, J=5.09 Hz, 1 H), 7.32-7.37 (m, 2 H), 7.29 (s, 1 H), 6.98 (s, 1 H), 6.56 (s, 1 H), 2.41 (s, 3 H), 1.53 (s, 9 H).

Workup

temperatureThe mixture was cooled to RT
washwashed with water
dry with materialthe organic layer was dried over anh. Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7cd6fecfb7e14f8bbfa60e3ebdb29ec5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187486B2

Reaction notes

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