Carbamate → 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid

HRID 2093055ノート

反応式

HRID 2093055 の反応式
Cl.C([O:4][C:5]([C:7]1[S:8][C:9]2[CH2:10][NH:11][CH2:12][CH2:13][C:14]=2[N:15]=1)=[O:6])C.CCN(CC)CC.[C:23](=[O:26])([O-])[NH2:24].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CO.O>[N:28]1[C:27]2[C:36](=[C:35]([NH:24][C:23]([N:11]3[CH2:12][CH2:13][C:14]4[N:15]=[C:7]([C:5]([OH:4])=[O:6])[S:8][C:9]=4[CH2:10]3)=[O:26])[CH:34]=[CH:33][CH:32]=2)[CH:31]=[CH:30][CH:29]=1

参加物

10

反応物 6

HCID 276CarbamateHCID 313Hydrochloric AcidHCID 8405IsoquinolineHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 53393419Ethyl 4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate

生成物 1

HCID 668650425-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

5-tert-butyl 2-ethyl 6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-2,5(4H)-dicarboxylate obtained in step V of example 1 was deprotected to get the hydrochloride salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester. To a solution of a HCl salt of 4,5,6,7-Tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid ethyl ester (1.0 eq) in DMF was added Et3N (1.0 eq.) followed by carbamate derivative of Isoquinoline (1.0 eq) obtained in step I above. The reaction mixture was refluxed for 3 h at 90° C. Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, was hydrolysed by stirring in MeOH: water and K2CO3 (2.0 eq.) for 48 h Reaction mixture was concentrated under reduced pressure and neutralized to pH 7.0 to afford 5-(Quinolin-5-ylcarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylic acid).

後処理

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford crude product, which
  5. concentrationwas concentrated under reduced pressure and neutralized to pH 7.0

出典と根拠

ORDレコード
ord-03ac15654a1a4d8daa08631d22333b15
出典データセット
uspto-grants-2013_05
特許番号
US08440830B2

反応ノート

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