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

HRID 1882158Notes

Reaction equation

HRID 1882158 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([O:13][CH:14]([F:16])[F:15])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:17]=[CH:18]/[C:19]2[N:20]=[C:21]3[N:25]([C:26]=2[C:27]([OH:29])=O)[CH:24]=[CH:23][S:22]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:30][C:31]([F:39])([F:38])[C:32]1[N:33]=[C:34]([NH2:37])[S:35][CH:36]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH:14]([F:16])[F:15])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:17]=[CH:18]/[C:19]2[N:20]=[C:21]3[N:25]([C:26]=2[C:27]([NH:37][C:34]2[S:35][CH:36]=[C:32]([C:31]([F:39])([F:38])[F:30])[N:33]=2)=[O:29])[CH:24]=[CH:23][S:22]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593699436-{(E)-2-[2-(Cyclopentyloxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468332516-{(E)-2-[2-Cyclopentyloxy-3-(difluoromethoxy)phenyl]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 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 5 (365 mg, 0.868 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (157 mg, 0.965 mmol) in the presence of EDCI hydrochloride (333 mg, 1.737 mmol) and DMAP (98 mg, 0.868 mmol) in a mixture of THF and DMF (1:1, 6 mL) to give 34 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.75-1.85 (m, 8H), 4.70-4.78 (m, 1H), 7.18 (t, J=74.7 Hz, 1H), 7.20-7.5 (m, 2H), 7.40-7.46 (m, 1H), 7.53 (d, J=15.9 Hz, 1H), 7.60-7.70 (m, 1H), 7.79 (d, J=15.0 Hz, 1H), 8.05-8.12 (m, 2H), 13.03 (br s, 1H); APCI-MS (m/z) 571.07 (MH)+.

Sources & evidence

ORD record
ord-2b773b2d62ce4f8abb1c59f1b9ec55e2
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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