Triethylamine → 2-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid

HRID 1984706

反応式

HRID 1984706 の反応式
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]=1.[SH:24][C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28].C(OCC)(=O)C>CN(C)C=O>[C:20]([O:19][C:17]([NH:16][C:12]1[CH:11]=[C:10]([CH2:9][S:24][C:25]2[C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=[CH:32][N:33]=2)[CH:15]=[CH:14][N:13]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 220977361,1-Dimethylethyl N-[4-(bromomethyl)-2-pyridinyl]carbamateHCID 178524460HCID 178524460、化合物

生成物 1

HCID 231509762-(2-tert-Butoxycarbonylaminopyridin-4-ylmethylthio)pyridine-3-carboxylic acid収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of triethylamine (0.75 mL, 5.4 mmol) in N,N-dimethylformamide (2.0 mL) was added to a solution of 4-bromomethyl-2-tert-butoxycarbonylaminopyridine (Reference compound No. 8-1, 500 mg, 1.7 mmol) and 2-mercaptonicotinic acid (270 mg, 1.7 mmol) in N,N-dimethylformamide (3.0 mL) under ice-cooling, and the mixture was stirred for 12 hours at room temperature. Ethyl acetate (20 mL) was added to the reaction mixture, and the whole was extracted with 0.1N aqueous sodium hydroxide solution (50 mL). 1N Hydrochloric acid was added to the aqueous layer to adjust to pH 5, and the precipitated crystal was filtered off. The crystal was dried under reduced pressure at 60° C. to give 560 mg of the title reference compound as a colorless crystal. (Yield 88%)

後処理

  1. extractionthe whole was extracted with 0.1N aqueous sodium hydroxide solution (50 mL)
  2. addition1N Hydrochloric acid was added to the aqueous layer
  3. filtrationthe precipitated crystal was filtered off
  4. customThe crystal was dried under reduced pressure at 60° C.
  5. customto give 560 mg of the title reference compound as a colorless crystal

出典と根拠

ORDレコード
ord-27456374c0c8432d940c7742997ad096
出典データセット
uspto-grants-2009_06
特許番号
US07544703B2

関連ノート

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