Phenylpropiolic Acid → 3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide

HRID 1880651노트

반응식

HRID 1880651 반응식
FC(F)(F)C(O)=O.[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[N:13]1[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.[C:20]1([C:26]#[C:27][C:28](O)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>ClCCCl>[C:20]1([C:26]#[C:27][C:28]([NH:19][CH:16]2[CH2:17][CH2:18][N:13]([C:9]3[S:8][CH:12]=[CH:11][N:10]=3)[CH2:14][CH2:15]2)=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 69475Phenylpropiolic AcidHCID 81531DiisopropylethylamineHCID 691528731-(Thiazol-2-yl)piperidin-4-amine trifluoroacetate

생성물 1

HCID 236492043-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide수율 51.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of 500 mg (1.68 mmol) 1-(thiazol-2-yl)piperidin-4-amine trifluoroacetate, 332 mg (2.02 mmol) 3-phenylpropiolic acid and 1.17 ml DIPEA in DCE (20 ml) was stirred for 5 h at RT. Subsequently, the reaction solution was washed with water and a sat. aqueous Na2CO3 soln and dried over MgSO4. After filtering and concentration in vacuo, column chromatography (SiO2, chloroform) was performed on the residue, yielding 267 mg (0.86 mmol, 51%) 3-phenyl-N-(1-(thiazol-2-yl)piperidin-4-yl)propiolamide. MS [MH+] 312.1

후처리

  1. washSubsequently, the reaction solution was washed with water
  2. dry with materiala sat. aqueous Na2CO3 soln and dried over MgSO4
  3. filtrationAfter filtering
  4. concentrationconcentration in vacuo, column chromatography (SiO2, chloroform)

출처 및 근거

ORD 기록
ord-2c1ff923552146468afc4db129fcd779
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318774B2

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