6-(Trifluoromethyl)nicotinic acid → 4-Methoxymethyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazole-5-carboxylic acid methyl ester

HRID 2233288노트

반응식

HRID 2233288 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][N:4]=1.FC(F)(F)C1C=CC(C(O)=O)=CN=1.ClCC1OC(C2(C)CCCCC2)=NC=1C.ClCC1SC(C2CCC(F)(F)CC2)=NC=1COC.[CH3:60][O:61][C:62](=[O:70])[CH:63](Cl)[C:64](=O)[CH2:65][O:66][CH3:67]>C(O)C>[CH3:60][O:61][C:62]([C:63]1[S:8][C:7]([C:6]2[CH:5]=[N:4][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:11][CH:10]=2)=[N:9][C:64]=1[CH2:65][O:66][CH3:67])=[O:70]

참가 물질

7

반응물 5

HCID 27775516-(Trifluoromethyl)nicotinic acidHCID 27778866-(Trifluoromethyl)thionicotinamideHCID 592953925-Chloromethyl-4-methyl-2-(1-methyl-cyclohexyl)-oxazoleHCID 59295416Methyl 2-chloro-4-methoxy-3-oxobutanoateHCID 592954495-Chloromethyl-2-(4,4-difluoro-cyclohexyl)-4-methoxymethyl-thiazole

생성물 1

HCID 592953904-Methoxymethyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazole-5-carboxylic acid methyl ester수율 11.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

10.5 g 6-Trifluoromethyl-thionicotinamide (derived from 6-Trifluoromethyl-nicotinic acid according to the method described for 5-Chloromethyl-4-methyl-2-(1-methyl-cyclohexyl)-oxazole and 5-Chloromethyl-2-(4,4-difluoro-cyclohexyl)-4-methoxymethyl-thiazole) and 10.0 g 2-Chloro-4-methoxy-3-oxo-butyric acid methyl ester were dissolved in 100 ml ethanol and heated under reflux overnight. The cooled reaction mixture was evaporated under reduced pressure and the resulting residue was purified by RP-HPLC to obtain 1.9 g 4-Methoxymethyl-2-(6-trifluoromethyl-pyridin-3-yl)-thiazole-5-carboxylic acid methyl ester.

후처리

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. customThe cooled reaction mixture
  4. customwas evaporated under reduced pressure
  5. customthe resulting residue was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-b4cfbf2419f242eaab6dffa4c6727eef
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709481B2

반응 노트

불러오는 중…