Ethyl orthoformate → HCID 86681220, compound

HRID 1848247Notes

Reaction equation

[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][NH:13][C:14]3[C:19]([NH2:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH2:25](OC(OCC)OCC)C>C(O)=O>[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][N:13]3[C:14]4=[N:15][CH:16]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:18]=[C:19]4[N:20]=[CH:25]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-5-(trifluoromethyl)pyridine-2,3-diamine (0.89 g, 2.39 mmol), triethoxymethane (30 mL) and HCOOH (0.6 g) was stirred at 90° C. for 2 h. The mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 2:1 to 0:1 petroleum ether/EtOAc to afford 2-(methylthio)-6-((6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazole as a light yellow solid (0.77 g, 79.3%). 1H NMR (300 MHz, DMSO-d6) δ 8.88 (s, 1H), 8.77 (d, J=1.2 Hz, 1H), 8.57 (d, J=1.8 Hz, 1H), 8.00 (d, J=1.2 Hz, 1H), 7.81 (d, J=8.4 Hz, 1H), 7.49-7.46 (m, 1H), 5.68 (s, 2H), 2.77 (s, 3H). LCMS (ESI) m/z 381 (M+H)+.

Workup

concentrationThe mixture was concentrated under reduced pressure
customThe residue was purified by silica gel chromatography
washeluting with 2:1 to 0:1 petroleum ether/EtOAc

Sources & evidence

ORD record: ord-b2a9c06b21e7474abaa31546ae47af36
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952058B2

Reaction notes

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