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

HRID 1882148Notes

Reaction equation

HRID 1882148 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([OH:26])=O)[CH:21]=[CH:20][S:19]3)[CH2:3][CH2:2]1.[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>[CH:1]1([CH2:4][O:5][C:6]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=2/[CH:14]=[CH:15]/[C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[C:24]([NH:34][C:31]2[S:32][CH:33]=[C:29]([C:28]([F:36])([F:35])[F:27])[N:30]=2)=[O:26])[CH:21]=[CH:20][S:19]3)[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 593698916-{(E)-2-[2-(Cyclopropylmethoxy)-3-methoxyphenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468323726-[(E)-2-(2-Cyclopropylmethoxy-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 1 (200 mg, 0.539 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (100 mg, 0.593 mmol) in the presence of EDCI hydrochloride (206 mg, 1.079 mmol) and DMAP (99 mg, 0.809 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 72 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 0.24-0.26 (m, 2H), 0.47-0.49 (m, 2H), 1.15-1.18 (m, 1H), 3.75 (d, J=6.9 Hz, 2H), 3.79 (s, 3H), 6.96-6.99 (m, 1H), 7.09 (t, J=7.8 Hz, 1H), 7.30-7.33 (m, 1H), 7.40-7.42 (m, 1H), 7.46 (d, J=15.6 Hz, 1H), 7.87 (d, J=15.6 Hz, 1H), 8.03 (s, 1H), 8.06 (d, J=4.2 Hz, 1H), 12.94 (s, 1H); ESI-MS (m/z) 521.34 (MH)+.

Sources & evidence

ORD record
ord-157c22aa11824eb2b100e98d7c68e050
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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