3,4,5,6-Tetrahydro-2H-cyclopenta(d)(1,3)thiazol-2-imine → HCID 46833852, compound

HRID 1882166Notes

Reaction equation

HRID 1882166 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]([OH:22])=O)[CH:17]=[CH:16][S:15]3)[CH:7]=[CH:8][CH:9]=1.[S:30]1[C:34]2[CH2:35][CH2:36][CH2:37][C:33]=2[N:32]=[C:31]1[NH2:38].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C1COCC1.CN(C=O)C>[CH3:26][C:25]([CH3:28])([CH3:27])[CH2:24][O:23][C:5]1[C:4]([O:3][CH:2]([F:29])[F:1])=[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:38][C:31]1[S:30][C:34]3[CH2:35][CH2:36][CH2:37][C:33]=3[N:32]=1)=[O:22])[CH:17]=[CH:16][S:15]2

Participants

7

Reactant 3

HCID 3322553,4,5,6-Tetrahydro-2H-cyclopenta(d)(1,3)thiazol-2-imineHCID 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 46833852HCID 46833852, 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 (100 mg, 0.236 mmol) with 5,6-dihydro-4H-cyclopenta[d][1,3]thiazol-2-amine (37 mg, 0.260 mmol) in the presence of EDCI hydrochloride (91 mg, 0.472 mmol) and DMAP (26 mg, 0.236 mmol) in a mixture of THF and DMF (1:1, 4 mL) to give 20 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.07 (s, 9H), 2.42-2.52 (m, 2H), 2.75-2.81 (m, 4H), 3.58 (s, 2H), 7.18 (t, J=76.2 Hz, 1H), 7.20-7.28 (m, 2H), 7.38-7.45 (m, 1H), 7.71 (d, J=6.9 Hz, 1H), 7.84 (d, J=15.9 Hz, 1H), 8.05-8.12 (m, 1H), 8.46-8.53 (m, 1H), 13.03 (br s, 1H); APCI-MS (m/z) 545.53 (MH)+.

Sources & evidence

ORD record
ord-8b864dec097e4d7e9ea80c2764ab0d29
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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