2-Thiazolamine, 4-(trifluoromethyl)- → HCID 46833250, compound

HRID 1882157Notes

Reaction equation

HRID 1882157 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:15]=[CH:16]/[C:17]2[N:18]=[C:19]3[N:23]([C:24]=2[C:25](O)=[O:26])[CH:22]=[CH:21][S:20]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:28][C:29]([F:37])([F:36])[C:30]1[N:31]=[C:32]([NH2:35])[S:33][CH:34]=1.CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl.CN(C=O)C>[CH:1]1([O:6][C:7]2[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[CH:9][C:8]=2/[CH:15]=[CH:16]/[C:17]2[N:18]=[C:19]3[N:23]([C:24]=2[C:25]([NH:35][C:32]2[S:33][CH:34]=[C:30]([C:29]([F:37])([F:36])[F:28])[N:31]=2)=[O:26])[CH:22]=[CH:21][S:20]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 12014172-Thiazolamine, 4-(trifluoromethyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59369919HCID 59369919, compound

Product 1

HCID 46833250HCID 46833250, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 4 (200 mg, 0.520 mmol) with 4-(trifluoromethyl)-1,3-thiazol-2-amine (105 mg, 0.624 mmol) in the presence of EDCI hydrochloride (200 mg, 1.040 mmol) and DMAP (159 mg, 1.300 mmol) in a mixture of DCM and DMF (4:1, 5 mL) to give 86 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 1.52-1.62 (m, 4H), 1.76-1.79 (m, 4H), 3.81 (s, 3H), 4.85 (br s, 1H), 7.00 (d, J=7.8 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.43-7.49 (m, 2H), 7.82 (d, J=16.2 Hz, 1H), 8.06-8.10 (m, 2H), 12.99 (br s, 1H); ESI-MS (m/z) 535.11 (MH)+.

Sources & evidence

ORD record
ord-a5447be918074785832ee330868a2053
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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