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

HRID 1483220

반응식

HRID 1483220 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-936824ed268141a19c4edc04c2fab9e6
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416141B2

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