1-Hydroxybenzotriazole → HCID 46945433, compound

HRID 467874Notes

Reaction equation

HRID 467874 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].[CH3:19][C:20]([CH3:38])([CH3:37])[CH2:21][O:22][C:23]1[C:28]([F:29])=[CH:27][C:26]([C:30]2[N:31]=[C:32]([NH2:35])[S:33][CH:34]=2)=[CH:25][C:24]=1[F:36].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[F:36][C:24]1[CH:25]=[C:26]([C:30]2[N:31]=[C:32]([NH:35][C:12](=[O:14])[CH2:11][C:10]3[C:6]4[C:5](=[O:16])[N:4]([CH3:17])[C:3](=[O:18])[N:2]([CH3:1])[C:7]=4[N:8]([CH3:15])[CH:9]=3)[S:33][CH:34]=2)[CH:27]=[C:28]([F:29])[C:23]=1[O:22][CH2:21][C:20]([CH3:38])([CH3:37])[CH3:19]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66742899HCID 66742899, compoundHCID 86662213HCID 86662213, compound

Product 1

HCID 46945433HCID 46945433, 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-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-amine (118 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 40 mg of the product as an off white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz) 1.01 (s, 9H), 3.21 (s, 3H), 3.73 (s, 3H), 3.80 (s, 5H), 3.93 (s, 2H), 6.35 (s, 1H), 7.64 (d, J=9.6 Hz, 2H), 7.67 (s, 1H), 12.53 (br s, 1H, exchangeable with D2O); ESI-MS (m/z) 532.24 (M+H)+.

Sources & evidence

ORD record
ord-07527d95c17a416dadc203e56f65df86
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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