Ethyl orthoformate → HCID 86681115, compound

HRID 1848145Notes

Reaction equation

HRID 1848145 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:15]([NH2:24])=[CH:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[CH:25](OCC)(OCC)OCC>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[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=4[N:24]=[CH:25]3)[CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 86681116HCID 86681116, compound

Product 1

HCID 86681115HCID 86681115, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-4-(trifluoromethyl)benzene-1,2-diamine (0.32 g, 0.86 mmol) from the previous step, formic acid (0.5 mL) and triethyl orthoformate (5 mL) was heated at 100° C. for 1 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 3% MeOH in DCM to afford 2-(methylthio)-6-((5-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazole (0.22 g, 69%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 8.12 (s, 1H), 8.08 (s, 1H), 7.84 (d, J=8.4 Hz, 1H), 7.48-7.54 (m, 2H), 7.36 (d, J=8.4 Hz, 1H), 7.26 (m, 1H), 5.49 (s, 2H), 2.78 (s, 3H); LCMS (ESI) m/z 380 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel flash chromatography
  4. washeluting with 3% MeOH in DCM

Sources & evidence

ORD record
ord-cd94bc20a3ee402f85b7f61d6da6b673
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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