Methanol → HCID 178482085, compound

HRID 2282115Notes

Reaction equation

HRID 2282115 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:26]#[N:27])=[C:11]([C:19]2[CH:24]=[CH:23][N:22]=[C:21](F)[CH:20]=2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1.[CH3:28][NH2:29].CO>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:26]#[N:27])=[C:11]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:29][CH3:28])[CH:20]=2)[S:12][C:13]=1[C:14]1[NH:18][CH:17]=[N:16][N:15]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 178509408HCID 178509408, compound

Product 1

HCID 178482085HCID 178482085, compoundYield 44%

Procedure

A solution of 4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile (0.100 g, 0.000240 mol) and 1M Methylamine in methanol (4 mL, 0.004 mol) 0.000163 mol) was heated at 80° C. for 5 hours. The solvent was removed and the residue was purified using a silica gel chromatography (12 g), elution DCM to 5% MeOH in DCM over 20 minutes to afford the title compound (0.045 g, 44%). LCMS: (FA) ES+, 427, 429. 1H NMR (400 MHz, d4-Methanol) 8.38 (s, 1H), 8.12-8.07 (m, 1H), 7.60 (dd, J=1.56, 0.77 Hz, 1H), 7.44-7.42 (m, 2H), 6.94 (dd, J=4.67, 1.66 Hz, 1H), 6.93 (s, 1H), 2.92 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified
  3. washa silica gel chromatography (12 g), elution DCM to 5% MeOH in DCM over 20 minutes

Sources & evidence

ORD record
ord-b7e1b2fe5a4b49d89dadd273bf610db0
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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