4-Cyclopropyl-1,3-thiazol-2-amine → HCID 46834416, compound

HRID 1882173Notes

Reaction equation

HRID 1882173 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][O:4][C:5]1[C:10]([O:11][CH:12]([F:14])[F:13])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:15]=[CH:16]/[C:17]1[N:18]=[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]2[C:25]=1[C:26]([OH:28])=O.[CH:31]1([C:34]2[N:35]=[C:36]([NH2:39])[S:37][CH:38]=2)[CH2:33][CH2:32]1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[CH3:1][C:2]([CH3:29])([CH3:30])[CH2:3][O:4][C:5]1[C:10]([O:11][CH:12]([F:13])[F:14])=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:15]=[CH:16]/[C:17]1[N:18]=[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]2[C:25]=1[C:26]([NH:39][C:36]1[S:37][CH:38]=[C:34]([CH:31]2[CH2:33][CH2:32]2)[N:35]=1)=[O:28]

Participants

7

Reactant 3

HCID 6744564-Cyclopropyl-1,3-thiazol-2-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675491302-{(E)-2-[2-(2,2-Dimethylpropoxy)-3-(difluoromethoxy)phenyl]vinyl}imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 46834416HCID 46834416, compound

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 13 (100 mg, 0.240 mmol) with 4-cyclopropyl-1,3-thiazol-2-amine (37 mg, 0.264 mmol) in the presence of EDCI hydrochloride (91 mg, 0.480 mmol) and DMAP (27 mg, 0.240 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 35 mg of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 0.79-0.85 (m, 2H), 1.05 (s, 9H), 1.20-1.26 (m, 2H), 1.95-2.01 (m, 1H), 3.58 (d, J=5.4 Hz, 2H), 6.60-6.71 (m, 1H), 6.90-6.98 (m, 1H), 7.10-7.27 (m, 3H), 7.38-7.46 (m, 1H), 7.50-7.56 (m, 2H), 7.63-7.70 (m, 1H), 7.92 (d, J=15.6 Hz, 1H), 7.99 (d, J=15.0 Hz, 1H), 13.03 (br s, 1H); APCI-MS (m/z) 539.45 (MH)+.

Sources & evidence

ORD record
ord-ba62ebf9f3954e2296de54a11d8fffa9
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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