2-Thiazolamine, 4-(trifluoromethyl)- → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882152Notes

Reaction equation

HRID 1882152 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[C:23](O)=[O:24])[CH:20]=[CH:19][S:18]2.[F:28][C:29]([F:37])([F:36])[C:30]1[N:31]=[C:32]([NH2:35])[S:33][CH:34]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH3:26][C:2]([CH3:1])([CH3:27])[CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:13]=[CH:14]/[C:15]1[N:16]=[C:17]2[N:21]([C:22]=1[C:23]([NH:35][C:32]1[S:33][CH:34]=[C:30]([C:29]([F:37])([F:36])[F:28])[N:31]=1)=[O:24])[CH:20]=[CH:19][S:18]2

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675494856-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 462139446-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]imidazo[2,1-b][1,3]thiazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 3 (200 mg, 0.517 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (105 mg, 0.621 mmol) in the presence of EDCI hydrochloride (198 mg, 1.035 mmol) and DMAP (95 mg, 0.776 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 114 mg of the product as a pale yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 1.01 (s, 9H), 3.56 (s, 2H), 3.80 (s, 3H), 6.98-6.99 (m, 1H), 7.11 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.43-7.48 (m, 2H), 7.85 (d, J=16.2 Hz, 1H), 8.05-8.09 (m, 2H), 12.97 (br s, 1H); ESI-MS (m/z) 535.20 (M−H)−.

Sources & evidence

ORD record
ord-368e9389056f499ba7d3787a713dca69
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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