7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one → 7-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1453193노트

반응식

HRID 1453193 반응식
Cl[CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[C:10]([CH3:13])[N:6]2[C:7](=[O:9])[CH:8]=1.ClCC1N(C)N=C(C)N=1.[Cl:23][C:24]1[C:25]([O:47][CH3:48])=[CH:26][C:27]([O:45][CH3:46])=[C:28]([CH2:30][CH2:31][C:32]2([CH:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[O:37][C:36](=[O:38])[CH2:35][C:34](=[O:39])[CH2:33]2)[CH:29]=1>>[Cl:23][C:24]1[C:25]([O:47][CH3:48])=[CH:26][C:27]([O:45][CH3:46])=[C:28]([CH2:30][CH2:31][C:32]2([CH:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[O:37][C:36](=[O:38])[C:35]([CH2:2][C:3]3[N:4]=[C:5]4[S:12][CH:11]=[C:10]([CH3:13])[N:6]4[C:7](=[O:9])[CH:8]=3)=[C:34]([OH:39])[CH2:33]2)[CH:29]=1

참가 물질

4

반응물 3

HCID 43541347-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneHCID 131031005-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazoleHCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione

생성물 1

HCID 587623847-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one수율 18%

실험 절차

The title compound was prepared as described in Example B(53), using 7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (prepared according to a reported procedure: Doria, G.; Passarotti, C.; Sala, R.; Magrini, R.; Sberze, P.; Tibolla, M.; Cesarani, R.; Arcari, G.; Castello, R.; Toti, D. Farmaco Ed. Sci. 1985, 40, 885) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 18%. 1H NMR (300 MHz, DMSO-d6) δ 1.23-1.73 (m, 8H), 1.78-2.0 (m, 2H), 2.35 (m, 1H), 2.48-2.58 (m, 2H, overlap with DMSO-d5), 2.64 (s, m, overlap, 4H), 2.78 (d, J=18 Hz, 1H), 3.44 (s, 2H), 3.78 (s, 3H, overlap with H2O peak), 3.85 (s, 3H), 5.80 (s, 1H), 6.70 (s, 1H), 6.97 (s, 1H), 7.11 (s, 1H), 10.96 (br s, 1H). LC-MS (APCI) calcd for C28H31ClN2O6S: 558.16; found (M+H+) 559.0 m/z.

후처리

  1. customprepared

출처 및 근거

ORD 기록
ord-f009c52a5eff45339c3280b9f75d5b41
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473790B2

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