2,2,2-Trifluoroethylamine hydrochloride → HCID 46834135, compound

HRID 1882169Notes

Reaction equation

HRID 1882169 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.Cl.[F:31][C:32]([F:36])([F:35])[CH2:33][NH2:34].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[F:1][CH:2]([F:29])[O:3][C:4]1[C:5]([O:23][CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[C:6](/[CH:10]=[CH:11]/[C:12]2[N:13]=[C:14]3[N:18]([C:19]=2[C:20]([NH:34][CH2:33][C:32]([F:36])([F:35])[F:31])=[O:21])[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 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 46834135HCID 46834135, 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 7A (80 mg, 0.189 mmol) with 2,2,2-trifluoroethanamine hydrochloride (28 mg, 0.208 mmol) in the presence of EDCI hydrochloride (72 mg, 0.378 mmol), DMAP (43 mg, 0.378 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 60 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 3.57 (s, 2H), 4.10-4.18 (m, 2H), 7.17 (t, J=74.7 Hz, 1H), 7.20 (d, J=7.5 Hz, 2H), 7.39-7.48 (m, 2H), 7.60-7.66 (m, 1H), 7.84 (d, J=15.6 Hz, 1H), 8.00 (s, 1H), 8.85 (br s, 1H); ESI-MS (m/z) 504.22 (MH)+.

Sources & evidence

ORD record
ord-6ffa56e78e944faf9249e033673eed1e
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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