1-Hydroxybenzotriazole → 1246761-03-4

HRID 877037Notes

Reaction equation

HRID 877037 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][S:9][C:10](C)=[C:6]2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[F:15][C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[C:20]([F:26])[CH:19]=[CH:18][C:17]=1[C:27]1[N:28]=[C:29]([NH2:32])[S:30][CH:31]=1.CCN=C=NC[CH2:39][CH2:40]N(C)C.Cl.C1C=CC2N([OH:54])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[F:15][C:16]1[C:21]([C:22]([F:23])([F:24])[F:25])=[C:20]([F:26])[CH:19]=[CH:18][C:17]=1[C:27]1[N:28]=[C:29]([NH:32][C:39](=[O:54])[CH2:40][C:7]2[C:6]3[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:10]=3[S:9][CH:8]=2)[S:30][CH:31]=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 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 469266991246761-03-4

Reagents, catalysts & solvents 2

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

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 4-[2,4-difluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (110 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.471 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (4 ml) to give 20 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.07 (s, 2H), 7.08 (s, 1H), 7.55 (t, J=9.0 Hz, 1H), 7.62 (s, 1H), 8.34 (q, J=6.9 Hz, 1H), 12.50 (br s, 1H); ESI-MS (m/z) 517.09 (M+H)+.

Sources & evidence

ORD record
ord-f2bc307977544408a3727d769a85370e
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Reaction notes

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