Tetrahydrofuran → HCID 46833855, compound

HRID 1882165Notes

Reaction equation

HRID 1882165 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:30][C:31]1[C:32]([NH2:41])=[N:33][CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1.CCN=C=NCCCN(C)C.Cl.C1COCC1>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:30][C:31]1[C:32]([NH:41][C:20]([C:19]2[N:18]3[C:14]([S:15][CH:16]=[CH:17]3)=[N:13][C:12]=2/[CH:11]=[CH:10]/[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:2]([F:29])[F:1])[C:5]=2[O:23][CH2:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:21])=[N:33][CH:34]=[C:35]([C:37]([F:40])([F:38])[F:39])[CH:36]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 6072483-Chloro-5-(trifluoromethyl)-2-pyridinamineHCID 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 46833855HCID 46833855, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7A (100 mg, 0.236 mmol) with 3-chloro-5-(trifluoromethyl)pyridin-2-amine (51 mg, 0.260 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol) and DMAP (27 mg, 0.236 mmol) in the mixture of THF and DMF (1:1, 6 mL) to give 25 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 3.57 (s, 2H), 7.16 (t, J=73.5 Hz, 1H), 7.20-7.46 (m, 3H), 7.53-7.62 (m, 2H), 7.88 (d, J=15.9 Hz, 1H), 8.09 (s, 1H), 8.57 (s, 1H), 8.86 (s, 1H), 11.12 (br s, 1H); APCI-MS (m/z) 601.30 (MH)+.

Sources & evidence

ORD record
ord-01b682b25e2c4a5b958eacefb47af0f4
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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