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

HRID 1880651ノート

反応式

HRID 1880651 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-2c1ff923552146468afc4db129fcd779
出典データセット
uspto-grants-2012_11
特許番号
US08318774B2

反応ノート

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