Triethylamine → 4-Methyloxycarbonylmethylaminophenyl [1-(4-pyridyl)piperidin-4-yl]acetate

HRID 1291880노트

반응식

HRID 1291880 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15]>ClCCl>[N:8]1[CH:5]=[CH:4][C:14]([N:16]2[CH2:19][CH2:20][CH:6]([CH2:7][C:2]([O:1][C:2]3[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=3)=[O:1])[CH2:18][CH2:17]2)=[CH:15][CH:9]=1

참가 물질

4

반응물 2

HCID 8471TriethylamineHCID 422581Methyl 2-((4-hydroxyphenyl)amino)acetate

생성물 1

HCID 196893984-Methyloxycarbonylmethylaminophenyl [1-(4-pyridyl)piperidin-4-yl]acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of the foam in dry dichloromethane (5 ml) was added dropwise to a stirred solution of methyl N-(4-hydroxyphenyl)glycinate (210 mg) and triethylamine (0.33 ml) in dry dichloromethane (10 ml) and the mixture stirred for 16 hours. The mixture was diluted with dichloromethane, washed with water, dried and evaporated. Purification by flash chromatography on silica, eluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether gave the title compound, 80 mg, as a white solid: m.p. 120°-122° C.; NMR(d6DMSO), δ 8.13(2H,d), 6.84(2H,d), 6.81(2H,d), 6.54(2H,d), 6.01(1H,t), 3.96(2H,bd), 3.90(2H,d), 3.66(3H,s), 2.90(2H,dt), 2.50(2H,d +DMSO), 2.07(1H,m), 1.81(2H,bd), 1.30(2H,dq); m/e 384(M+H)+ ; calculated for C21 H25N3O4. 0.5 H2O: C, 64.3; H, 6.6; N, 10.7. found: C, 64.2; H, 6.3; N, 10.7%.

후처리

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customPurification by flash chromatography on silica
  5. washeluting with 0-10% v/v methanol/dichloromethane and trituration of the resulting gum with diethyl ether

출처 및 근거

ORD 기록
ord-a5d2c43c4b0c4bddb525bc809af658b9
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753659

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