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

HRID 1882155Notes

Reaction equation

HRID 1882155 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[S:34][C:33]([NH2:35])=[N:32][N:31]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[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]([NH:35][C:33]1[S:34][C:30]([C:29]([F:37])([F:36])[F:28])=[N:31][N:32]=1)=[O:24])[CH:20]=[CH:19][S:18]2

Participants

7

Reactant 3

HCID 826341,3,4-Thiadiazol-2-amine, 5-(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 468329546-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-methoxyphenyl]vinyl}-N-[5-(trifluoromethyl)-1,3,4-thiadiazol-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 (150 mg, 0.388 mmol) with 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine (78 mg, 0.465 mmol) in the presence of EDCI hydrochloride (148 mg, 0.776 mmol) and DMAP (71 mg, 0.582 mmol) in a mixture of DCM and DMF (4:1, 10 mL) to give 80 mg of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 1.02 (s, 9H), 3.56 (s, 2H), 3.83 (s, 3H), 6.79-6.82 (m, 2H), 6.84-6.94 (m, 2H), 7.28 (d, J=16.5 Hz, 1H), 7.66 (d, J=15.9 Hz, 1H), 8.11 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 538.27 (MH)+.

Sources & evidence

ORD record
ord-0942fb531d4e43389ce562a834a0123b
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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