1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-cyclobutyl-1,3-thiazol-2-yl)imidazo[2,1-b][1,3]thiazole-5-carboxamide

HRID 1882161Notes

Reaction equation

HRID 1882161 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:34]2[N:35]=[C:36]([NH2:39])[S:37][CH:38]=2)[CH2:33][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]([CH3:26])([CH3:28])[CH2:24][O:23][C:5]1[C:4]([O:3][CH:2]([F:1])[F:29])=[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:39][C:36]1[S:37][CH:38]=[C:34]([CH:30]3[CH2:33][CH2:32][CH2:31]3)[N:35]=1)=[O:21])[CH:17]=[CH:16][S:15]2

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220636344-Cyclobutyl-1,3-thiazol-2-amineHCID 684073456-{(E)-2-[3-(Difluoromethoxy)-2-(2,2-dimethylpropoxy)phenyl]vinyl}imidazo[2,1-b][1,3]thiazole-5-carboxylic acid

Product 1

HCID 468335596-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}-N-(4-cyclobutyl-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-(cyclobutyl)-1,3-thiazol-2-amine (40 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), DMAP (26 mg, 0.236 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 50 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 1.84-1.90 (m, 2H), 1.95-2.05 (m, 1H), 2.15-2.30 (m, 4H), 3.58 (s, 2H), 6.73 (s, 1H), 7.18 (t, J=75.0 Hz, 1H), 7.20-7.30 (m, 2H), 7.38-7.44 (m, 1H), 7.66-7.72 (m, 1H), 7.83 (d, J=16.2 Hz, 1H), 8.10-8.18 (m, 1H), 8.62-8.68 (m, 1H), 12.87 (br s, 1H); ESI-MS (m/z) 559.22 (MH)+.

Sources & evidence

ORD record
ord-4f865578379e4dc9b31d2a7e2e840662
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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