Acetaldehyde → 6-Ethyl-2-(ethylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483220

反応式

HRID 1483220 の反応式
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:13]([NH2:15])=[O:14].[CH:16](=O)[CH3:17].S([O-])([O-])(=O)=O.[Mg+2].C([BH3-])#N.[Na+]>C(O)(=O)C.CO.O1CCCC1>[CH2:10]([N:7]1[CH2:8][CH2:9][C:4]2[C:3]([C:13]([NH2:15])=[O:14])=[C:2]([NH:1][CH2:16][CH3:17])[S:12][C:5]=2[CH2:6]1)[CH3:11]

参加物

8

反応物 4

HCID 177AcetaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6144392-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamideHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 680592166-Ethyl-2-(ethylamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide収率 80.4%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred mixture of compound F4 (200 mg, 0.888 mmol), acetaldehyde (5 M in tetrahydrofuran, 0.360 mL, 1.80 mmol), acetic acid (two drops), anhydrous magnesium sulfate (200 mg) in anhydrous methanol (6 mL) and anhydrous tetrahydrofuran (3 mL) was added sodium cyanoborohydride (167 mg, 2.66 mmol) at room temperature under nitrogen. The reaction mixture was stirred for 23 h and then filtered. The filtrate was concentrated. The resulting residue was purified by flash column chromatography on silica gel eluting with 10% to 20% methanol/methylene chloride to afford compound R1 as a colourless syrup (181 mg, 80%): MS (M+H) 254.

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customThe resulting residue was purified by flash column chromatography on silica gel eluting with 10% to 20% methanol/methylene chloride

出典と根拠

ORDレコード
ord-936824ed268141a19c4edc04c2fab9e6
出典データセット
uspto-grants-2016_08
特許番号
US09416141B2

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