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

HRID 1713118노트

반응식

HRID 1713118 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-77d14153a3b94344a3ffced9f4fd8fca
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795262B2

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