1-Hydroxybenzotriazole → 2-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

HRID 877030

Reaction equation

HRID 877030 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[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]([NH2:27])[S:25][CH:26]=2)=[CH:18][C:17]=1[C:28]([F:31])([F:30])[F:29].CCN=C=NC[CH2:38][CH2:39]N(C)C.Cl.C1C=CC2N([OH:53])N=NC=2C=1>CN(C1C=CN=CC=1)C.ClCCCl>[CH3:1][N:2]1[C:10]2[S:9][CH:8]=[C:7]([CH2:38][C:39]([NH:27][C:24]3[S:25][CH:26]=[C:22]([C:19]4[CH:20]=[CH:21][C:16]([F:15])=[C:17]([C:28]([F:29])([F:31])[F:30])[CH:18]=4)[N:23]=3)=[O:53])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 444498424-(4-Fluoro-3-(trifluoromethyl)phenyl)thiazol-2-amineHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 469277732-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

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 (102 mg, 0.401 mmol) with 4-[4-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (105 mg, 0.401 mmol) in the presence of EDCI hydrochloride (92 mg, 0.481 mmol), HOBt (16 mg, 0.120 mmol) and DMAP (5 mg, 0.040 mmol) in 1,2 dichloroethane (4 ml) to give 23 mg of the product as a white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.06 (s, 2H), 7.07 (s, 1H), 7.64 (t, J=9.0 Hz, 1H), 7.83 (s, 1H), 8.08-8.36 (m, 2H), 12.48 (br s, 1H); ESI-MS (m/z) 499.10 (M+H)+.

Sources & evidence

ORD record
ord-ee5e60b60e494ffeb6c7977dbe7aefc0
Source dataset
uspto-grants-2015_03
Patent number
US08987278B2

Linked notes

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