Ammonia → HCID 178509410, compound

HRID 2282113Notes

Reaction equation

HRID 2282113 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.[NH3:28].CO>>[NH2:28][C:21]1[CH:20]=[C:19]([C:11]2[S:12][C:13]([C:14]3[NH:18][CH:17]=[N:16][N:15]=3)=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:10]=2[C:26]#[N:27])[CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 178509408HCID 178509408, compound

Product 1

HCID 178509410HCID 178509410, compoundYield 44%

Procedure

A mixture of 4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)-5-(4H-1,2,4-triazol-3-yl)thiophene-3-carbonitrile (0.600 g, 0.00144 mol) and 7 M ammonia in methanol (40 mL, 0.280 mol) was irradiated in a microwave at 150° C. for 8 hours. Solvent was evaporated and the residue was purified by column chromatography on silica gel (40 g), gradient DCM to 6% MeOH in DCM over 30 minutes to afford the title compound as yellow solid (0.26 g, 44%). LCMS: (FA) ES+, 413, 415. 1H NMR (400 MHz, d4-Methanol) 8.40 (s, 1H), 8.05 (dd, J=5.16, 1.10 Hz, 1H), 7.61 (dd, J=1.54, 0.76 Hz, 1H), 7.46-7.42 (m, 2H), 7.03-7.00 (m, 2H)

Workup

  1. customwas irradiated in a microwave at 150° C. for 8 hours
  2. customSolvent was evaporated
  3. customthe residue was purified by column chromatography on silica gel (40 g), gradient DCM to 6% MeOH in DCM over 30 minutes

Sources & evidence

ORD record
ord-cc3e3d1f279b4467be6c27eddf5e4c93
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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