1-Hydroxybenzotriazole → HCID 46945435, compound

HRID 467876Notes

Reaction equation

HRID 467876 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[CH:21]=[C:22]([C:33]2[N:34]=[C:35]([NH2:38])[S:36][CH:37]=2)[CH:23]=[C:24]([F:32])[C:25]=1[O:26][CH2:27][C:28]([F:31])([F:30])[F:29].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[CH:21]=[C:22]([C:33]2[N:34]=[C:35]([NH:38][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:36][CH:37]=2)[CH:23]=[C:24]([F:32])[C:25]=1[O:26][CH2:27][C:28]([F:31])([F:29])[F:30]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57461659HCID 57461659, compoundHCID 66742899HCID 66742899, compound

Product 1

HCID 46945435HCID 46945435, 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-[3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-amine (123 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 70 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), 3.80 (s, 5H), 3.94 (s, 2H), 4.85 (q, J=8.7 Hz, 2H), 6.35 (s, 1H), 7.69 (d, J=9.3 Hz, 2H), 7.82 (s, 1H), 12.55 (br s, 1H, exchangeable with D2O); ESI-MS (m/z) 544.11 (M+H)+.

Sources & evidence

ORD record
ord-d962c7ae2be44be2bc6f3e1b6cdeeac0
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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