Water → HCID 178474053, compound

HRID 2282296Notes

Reaction equation

HRID 2282296 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:24]=2)[S:12][C:13]=1[C:14]1[NH:15][CH:16]=[C:17]([C:19](F)(F)F)[N:18]=1.O.[OH-].[NH4+:35]>>[C:19]([C:17]1[N:18]=[C:14]([C:13]2[S:12][C:11]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:24]=3)=[N:10][C:9]=2[C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[NH:15][CH:16]=1)#[N:35]

Participants

4

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 178474052HCID 178474052, compound

Product 1

HCID 178474053HCID 178474053, compoundYield 20%

Conditions

Temperature
60 °C

Procedure

N-(4-{4-(2,4-dichlorophenyl)-5-[4-(trifluoromethyl)-1H-imidazol-2-yl]-1,3-thiazol-2-yl}pyridin-2-yl)acetamide (20 mg, 0.04 mmol) was taken up in 1 M of Ammonium hydroxide in water (2 mL, 3 mmol) and the mixture was stirred at 60° C. for 6 h. At that time, LCMS indicated complete conversion. Reaction mixture was evaporated under reduced pressure and was purified using preparative HPLC to give 0.004 g of the title compound (20%). LCMS: (FA) ES+ 455, 457. 1H NMR (400 MHz, d6-DMSO) 8.70 (s, 1H), 8.34 (dd, J=5.26, 0.71 Hz, 1H), 7.65 (dd, J=5.26, 1.60 Hz, 1H), 7.55-7.46 (m, 3H), 7.39 (dd, J=8.28, 2.06 Hz, 1H), 2.24 (s, 3H).

Workup

  1. customReaction mixture
  2. customwas evaporated under reduced pressure
  3. customwas purified

Sources & evidence

ORD record
ord-b230ddd91c744fbfb6f6de0889717dcb
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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