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

HRID 877033

反応式

HRID 877033 の反応式
[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])=[CH:20][CH:19]=[CH:18][C:17]=1[C:26]1[N:27]=[C:28]([NH2:31])[S:29][CH:30]=1.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:31][C:28]3[S:29][CH:30]=[C:26]([C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([C:22]([F:23])([F:25])[F:24])[C:16]=4[F:15])[N:27]=3)=[O:53])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 120940524-(2-Fluoro-3-(trifluoromethyl)phenyl)thiazol-2-amineHCID 710080931,3,5-trimethylthieno[3,4-d]pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 469278412-(1,3-Dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-5-yl)-N-{4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}acetamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 111,2-Dichloroethane溶媒

実験手順

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (100 mg, 0.393 mmol) with 4-[2-fluoro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine (103 mg, 0.393 mmol) in the presence of EDCI hydrochloride (90 mg, 0.472 mmol), HOBt (16 mg, 0.117 mmol) and DMAP (5 mg, 0.039 mmol) in 1,2 dichloroethane (6 ml) to give 40 mg of the product as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 3.19 (s, 3H), 3.47 (s, 3H), 4.08 (s, 2H), 7.07 (s, 1H), 7.53 (t, J=7.5 Hz, 1H), 7.66 (s, 1H), 7.77 (t, J=6.9 Hz, 1H), 8.30-8.37 (m, 1H), 12.49 (br s, 1H); APCI-MS (m/z) 499.51 (M+H)+.

出典と根拠

ORDレコード
ord-639d6cb06b40484c87c91dcb8daefe4b
出典データセット
uspto-grants-2015_03
特許番号
US08987278B2

関連ノート

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