Methyl 2-aminopyridine-4-carboxylate → 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

HRID 50385

반응식

HRID 50385 반응식
[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11](O)=[O:12])=[CH:10][C:5]2=[N:4][C:3]=1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.BrC(C)C(=O)C=CC1C=CC(C#N)=CC=1.NC1C=C(C(OC)=O)C=CN=1.[CH2:50]([O:52][C:53]([CH2:55][CH2:56][NH:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)=[O:54])[CH3:51].C(OCC)(=O)C.C(O)C.N>S(Cl)(Cl)=O>[C:58]1([N:57]([CH2:56][CH2:55][C:53]([O:52][CH2:50][CH3:51])=[O:54])[C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([CH3:1])=[C:3]([CH2:14][CH2:15][C:16]4[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=4)[N:4]=[C:5]3[CH:10]=2)=[O:12])[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1

참가 물질

7

반응물 5

HCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 10910393beta-Alanine, N-phenyl-, ethyl esterHCID 184123193-Methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acidHCID 542928874-Bromo-1-(4-cyanophenyl)-1-penten-3-oneHCID 86587043Ethyl acetate ethanol ammonia

생성물 1

HCID 184123873-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid-N-phenyl-N-(2-ethoxycarbonylethyl)amide

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

1.4 g (4.6 mmol) of 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[1,2-a]pyridin-7-yl-carboxylic acid (prepared from 4-bromo-l-(4-cyanophenyl)-1-penten-3-one and methyl 2-aminopyridine-4-carboxylate analogously to Y. Katsura et al., Chem. Pharm. Bull. 1992, 40, 1424-1438) were suspended in 15 mL of thionyl chloride and heated to boiling for 1 hour until fully dissolved. After the thionyl chloride had been distilled off, the acid chloride was dissolved in 15 mL of pyridine without any further purification and at 0° C. mixed with 1.0 g (5.2 mmol) of N-(2-ethoxycarbonylethyl)aniline. After 1 hour, the solvent was distilled off, the residue was taken up in 30 mL of methylene chloride, washed with 15 mL of 1N hydrochloric acid, and dried with sodium sulfate. After distillation of the solvent and chromatography (silica gel; methylene chloride/ethanol=0 to 2%), a brown oil was obtained. Yield: 1.48 g (64% of theory); Rf value: 0.73 (silica gel; ethyl acetate/ethanol/ammonia=90:10:1).

후처리

  1. temperatureheated
  2. dissolutionuntil fully dissolved
  3. distillationAfter the thionyl chloride had been distilled off
  4. dissolutionthe acid chloride was dissolved in 15 mL of pyridine without any further purification and at 0° C.
  5. waitAfter 1 hour
  6. distillationthe solvent was distilled off
  7. washwashed with 15 mL of 1N hydrochloric acid
  8. dry with materialdried with sodium sulfate
  9. distillationAfter distillation of the solvent and chromatography (silica gel; methylene chloride/ethanol=0 to 2%)
  10. customa brown oil was obtained

출처 및 근거

ORD 기록
ord-d8e2acce4bec4d62bba9abbf288ea55d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710055B2

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