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

HRID 2233288ノート

反応式

HRID 2233288 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b4cfbf2419f242eaab6dffa4c6727eef
出典データセット
uspto-grants-2010_05
特許番号
US07709481B2

反応ノート

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