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Hydrochloric Acid → 2-[2-(Acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylic acid

HRID 2282312
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HRID 2282312 반응식
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:23]([O:25]CC)=[O:24])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:15]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[S:12][C:13]([C:23]([OH:25])=[O:24])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[N:15]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58095112Ethyl 2-[2-(acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylate

생성물 1

HCID 580949642-[2-(Acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylic acid수율 100.1%

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

To a stirred solution of ethyl 2-[2-(acetylamino)pyridin-4-yl]-4-(2-chlorophenyl)-1,3-thiazole-5-carboxylate (0.249 g, 0.620 mmol) in tetrahydrofuran (1.670 mL) and water (0.100 mL) was added lithium hydroxide, monohydrate (0.037 g, 0.891 mmol) and stirred for 18 h. The mixture was acidified to pH 6 with aqueous 1N HCl (1.20 mL, 1.20 mmol) and extracted with EtOAc (10.0 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude product (0.232 g) as a yellow solid and used without further purification. LC/MS (AA) ES+ 374, 376. 1H NMR (400 MHz, d6 DMSO) δ: 10.75 (br s, 1H), 8.69 (br s, 1H), 8.47-8.46 (m, 0.5H), 8.06-8.04 (m, 0.5H), 7.65-7.64 (m, 0.5H), 7.58-7.44 (m, 5H), 7.06-7.99 (m, 0.5H), 2.12 (s, 3H).

후처리

  1. extractionextracted with EtOAc (10.0 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a8abfd48cbfa4ac09f0533c9237071bc
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139589B2

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