2-Thiazolamine, 4-(trifluoromethyl)- → HCID 46834136, compound

HRID 1882170Notes

Reaction equation

HRID 1882170 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([OH:22])=O)[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=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>[F:29][CH:2]([F:1])[O:3][C:4]1[C:5]([O:23][CH2:24][CH2:25][CH:26]([CH3:27])[CH3:28])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([NH:37][C:34]2[S:35][CH:36]=[C:32]([C:31]([F:39])([F:38])[F:30])[N:33]=2)=[O:22])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59369897HCID 59369897, compound

Product 1

HCID 46834136HCID 46834136, 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 8 (300 mg, 0.710 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (128 mg, 0.781 mmol) in the presence of EDCI hydrochloride (272 mg, 1.42 mmol), DMAP (80 mg, 0.710 mmol) in a mixture of THF and DMF (1:1, 6 mL) to give 35 mg of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 0.86 (d, J=6.6 Hz, 6H), 1.56-1.65 (m, 2H), 1.77-1.86 (m, 1H), 3.95 (t, J=6.3 Hz, 2H), 7.20 (t, J=74.4 Hz, 1H), 7.22-7.30 (m, 2H), 7.46 (s, 1H), 7.57-7.64 (m, 2H), 7.76 (d, J=15.9 Hz, 1H), 8.05-8.12 (m, 2H), 13.03 (br s, 1H); APCI-MS (m/z) 573.23 (MH)+.

Sources & evidence

ORD record
ord-62421dc5055b417d8f3b6513380e2eb4
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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