Propynamide → 6-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

HRID 1713118ノート

反応式

HRID 1713118 の反応式
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([N:14]2[CH2:18][CH2:17][CH2:16]C2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N)(=[O:22])C#C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]2[NH:14][C:18](=[O:22])[CH:17]=[CH:16][C:12]=2[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 101445PropynamideHCID 117468121-Benzyl-4-(1-pyrrolidinyl)-1,2,3,6-tetrahydropyridine

生成物 1

HCID 223351456-Benzyl-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-benzyl-4-pyrrolidin-1-yl-1,2,3,6-tetrahydropyridine (2.58 g, 10.65 mmol) in toluene (30 mL) is added propiolamide (1.47 g, 21.29 mmol) and the mixture is refluxed for 4 hr. The mixture is cooled to rt and the solvent is removed in vacuo. The residue is partitioned between NaHCO3 (30 mL) and DCM (30 mL). The layers are separated and the aqueous layer is extracted with DCM (30 ml). The combined extracts are dried and evaporated and the residue is purified by flash column with 5% MeOH in DCM to give the title compound as a light yellow solid. MS (M+1): 241.1.

後処理

  1. temperaturethe mixture is refluxed for 4 hr
  2. customthe solvent is removed in vacuo
  3. customThe residue is partitioned between NaHCO3 (30 mL) and DCM (30 mL)
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with DCM (30 ml)
  6. customThe combined extracts are dried
  7. customevaporated
  8. customthe residue is purified by flash column with 5% MeOH in DCM

出典と根拠

ORDレコード
ord-77d14153a3b94344a3ffced9f4fd8fca
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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