Potassium Carbonate → HCID 11386033, compound

HRID 227664Notes

Reaction equation

HRID 227664 reaction equation
N1(C2SC(C(N)=O)=C(OCC3C=CC=CC=3C(F)(F)F)N=2)C2C=CC=CC=2N=C1.Cl[C:31]1[S:32][C:33]([C:48]([NH2:50])=[O:49])=[C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[C:44]([F:47])([F:46])[F:45])[N:35]=1.[CH3:51][O:52][C:53]1[C:61]([O:62][CH3:63])=[CH:60][C:56]2[N:57]=[CH:58][NH:59][C:55]=2[CH:54]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:63][O:62][C:61]1[C:53]([O:52][CH3:51])=[CH:54][C:55]2[N:59]([C:31]3[S:32][C:33]([C:48]([NH2:50])=[O:49])=[C:34]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=4[C:44]([F:47])([F:46])[F:45])[N:35]=3)[CH:58]=[N:57][C:56]=2[CH:60]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 6012215,6-DimethoxybenzimidazoleHCID 115389692-(1H-Benzimidazol-1-yl)-4-({[2-(trifluoromethyl)phenyl]methyl}-oxy)-1,3-thiazole-5-carboxamideHCID 57756681HCID 57756681, compound

Product 1

HCID 11386033HCID 11386033, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a manner analogous to the procedure described above for the preparation of 2-(1H-benzimidazol-1-yl)-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxamide, using the following materials: 2-chloro-4-({[2-(trifluoromethyl)phenyl]methyl}oxy)-1,3-thiazole-5-carboxamide (0.146 g, 0.434 mmol), 5,6-dimethoxybenzimidazole (0.0851 g, 0.478 mmol), K2CO3 (0.0720 g, 0.521 mmol) and DMF (4 mL). Flash chromatography afforded 0.114 g (55%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.75 (s, 1H), 7.87-7.73 (m, 4H), 7.61 (m, 1H), 7.61 (s, 1H), 7.37 (s, 1H), 6.94 (br s, 1H), 5.85 (s, 2H), 3.83 (s, 3H), 3.72 (s, 3H). MS m/z 479 (m+1).

Workup

  1. customThe title compound was prepared in a manner analogous to the procedure

Sources & evidence

ORD record
ord-0dbe8689c3b7436696d329a608d83b03
Source dataset
uspto-grants-2009_07
Patent number
US07560568B2

Reaction notes

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