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

HRID 1882151Notes

Reaction equation

HRID 1882151 reaction equation
[CH2:1]([O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:14]=[CH:15]/[C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24](O)=[O:25])[CH:21]=[CH:20][S:19]2)[CH:2]([CH3:4])[CH3:3].[F:27][C:28]([F:36])([F:35])[C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH2:1]([O:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1/[CH:14]=[CH:15]/[C:16]1[N:17]=[C:18]2[N:22]([C:23]=1[C:24]([NH:34][C:31]1[S:32][CH:33]=[C:29]([C:28]([F:36])([F:35])[F:27])[N:30]=1)=[O:25])[CH:21]=[CH:20][S:19]2)[CH:2]([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593698956-{(E)-2-[2-(Isobutoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468326566-{(E)-2-[2-(Isobutoxy)-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 2 (150 mg, 0.403 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (79 mg, 0.484 mmol) in the presence of EDCI hydrochloride (154 mg, 0.807 mmol) and DMAP (73 mg, 0.605 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 10 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.97 (d, J=6.3 Hz, 6H), 1.98-2.04 (m, 2H), 3.65-3.71 (m, 2H), 3.81 (s, 3H), 6.97-7.03 (m, 1H), 7.07-7.14 (m, 1H), 7.30-7.36 (m, 1H), 7.42-7.52 (m, 2H), 7.83 (d, J=16.2 Hz, 1H), 7.97-8.07 (m, 2H), 13.00 (br s, 1H); APCI-MS (m/z) 523.12 (MH)+.

Sources & evidence

ORD record
ord-27b88c98f3fe4800b0cca0c6aae12430
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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