1-Hydroxybenzotriazole → HCID 46945434, compound

HRID 467875Notes

Reaction equation

HRID 467875 reaction equation
[CH3:1][N:2]1[C:7]2[N:8]([CH3:15])[CH:9]=[C:10]([CH2:11][C:12]([OH:14])=O)[C:6]=2[C:5](=[O:16])[N:4]([CH3:17])[C:3]1=[O:18].[F:19][C:20]1[C:25]([C:26]([F:29])([F:28])[F:27])=[C:24]([F:30])[CH:23]=[CH:22][C:21]=1[C:31]1[N:32]=[C:33]([NH2:36])[S:34][CH:35]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[F:19][C:20]1[C:25]([C:26]([F:27])([F:28])[F:29])=[C:24]([F:30])[CH:23]=[CH:22][C:21]=1[C:31]1[N:32]=[C:33]([NH:36][C:12](=[O:14])[CH2:11][C:10]2[C:6]3[C:5](=[O:16])[N:4]([CH3:17])[C:3](=[O:18])[N:2]([CH3:1])[C:7]=3[N:8]([CH3:15])[CH:9]=2)[S:34][CH:35]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574616514-[2,4-Difluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amineHCID 66742899HCID 66742899, compound

Product 1

HCID 46945434HCID 46945434, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The title compound was prepared according to the general procedure (Method B) by coupling Intermediate 7 (100 mg, 0.398 mmol) with 4-[2,4-difluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (111 mg, 0.398 mmol) in the presence of EDCI hydrochloride (91 mg, 0.475 mmol), HOBt (16 mg, 0.118 mmol) and DMAP (4 mg, 0.032 mmol) in 1,2-dichloroethane (5 mL) to give 35 mg of the product as an off white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz) 3.21 (s, 3H), 3.73 (s, 3H), 3.81 (s, 3H), 3.95 (s, 2H), 6.35 (s, 1H), 7.51 (d, J=9.9 Hz, 1H), 8.32 (q, J=6.3 Hz, 1H), 12.61 (br s, 1H, exchangeable with D2O); ESI-MS (m/z) 514.09 (M+H)+.

Sources & evidence

ORD record
ord-c3fb50abe5ce426fa2147612e1bf22f3
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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