4-Cyclopropyl-1,3-thiazol-2-amine → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-cyclo-propyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882162Notes

Reaction equation

HRID 1882162 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20](O)=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.[CH:30]1([C:33]2[N:34]=[C:35]([NH2:38])[S:36][CH:37]=2)[CH2:32][CH2:31]1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[CH3:27][C:25]([CH3:28])([CH3:26])[CH2:24][O:23][C:5]1[C:4]([O:3][CH:2]([F:29])[F:1])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:10]=[CH:11]/[C:12]1[N:13]=[C:14]2[N:18]([C:19]=1[C:20]([NH:38][C:35]1[S:36][CH:37]=[C:33]([CH:30]3[CH2:32][CH2:31]3)[N:34]=1)=[O:21])[CH:17]=[CH:16][S:15]2

Participants

7

Reactant 3

HCID 6744564-Cyclopropyl-1,3-thiazol-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468335606-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-cyclo-propyl-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 7A (100 mg, 0.236 mmol) with 4-(cyclopropyl)-1,3-thiazol-2-amine (36 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol) and DMAP (26 mg, 0.236 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 40 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ0.80-0.86 (m, 2H), 1.06 (s, 9H), 1.13-1.23 (m, 2H), 1.94-2.00 (m, 1H), 3.57 (s, 2H), 6.60-6.66 (m, 1H), 7.18 (t, J=74.7 Hz, 1H), 7.22-7.30 (m, 2H), 7.40-7.48 (m, 1H), 7.68 (d, J=7.5 Hz, 1H), 7.82 (d, J=15.6 Hz, 1H), 8.08-8.16 (m, 1H), 8.52-8.60 (m, 1H), 12.99 (br s, 1H); APCI-MS (m/z) 545.18 (MH)+.

Sources & evidence

ORD record
ord-e3c1b2a138ff413e87ef0ba0fd852a28
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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