Triethylamine → HCID 18321803, 화합물

HRID 613615노트

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HRID 613615 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]2[N:15]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][O:27][C:28]4[CH:29]=[CH:30][CH:31]=[C:32]5[C:37]=4[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]5)[C:20]=3[Cl:39])[CH:16]=[CH:17][CH:18]=2)=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:48][C:49]1[N:57]=[CH:56][CH:55]=[CH:54][C:50]=1[C:51](Cl)=[O:52]>ClCCl>[Cl:39][C:20]1[C:21]([CH2:26][O:27][C:28]2[CH:29]=[CH:30][CH:31]=[C:32]3[C:37]=2[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]3)=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[N:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]1[CH:6]=[N:7][C:2]([NH:1][C:51](=[O:52])[C:50]2[CH:54]=[CH:55][CH:56]=[N:57][C:49]=2[CH3:48])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18321779HCID 18321779, 화합물HCID 183219202-Methylnicotinoyl chloride hydrochloride

생성물 1

HCID 18321803HCID 18321803, 화합물수율 67.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2-[(E)-3-(6-aminopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (152 mg) and triethylamine (96 mg) in dichloromethane (3 ml) was added 2-methylnicotinoyl chloride hydrochloride (115 mg) under nitrogen in ice water bath and stirred for 1 hour at the same temperature. The reaction solvent was concentrated in vacuo and the residue was dissolved in methanol. To the solution was added 1M sodium hydroxide solution (0.5 ml) and stirred for 30 minutes. The solution was evaporated and partitioned between chloroform and water. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography on silica gel (ethyl acetate) to give 1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]-2-[(E)-3-[6-[2-methylnicotinamido]pyridin-3-yl]acryloylaminomethyl]pyrrole (124 mg) as an amorphous powder. NMR (DMSO6, δ): 2.57 (3H, s), 4.26 (3H, s), 4.06-4.17 (1H, m), 4.21-4.33 (1H, m), 5.35-5.47 (2H, m), 6.18-6.25 (2H, m), 6.63 (1H, d, J=16 Hz), 6.85-6.90 (1H, m), 7.24 (1H, d, J=8 Hz), 7.29-7.36 (2H, m), 7.36-7.47 (3H, m), 7.53 (1H, d, J=8 Hz), 7.64 (1H, d, J=8 Hz), 7.73 (1H, d, J=8 Hz), 7.88 (1H, d, J=8 Hz), 8.03 (1H, d, J=8 Hz), 8.16-8.31 (3H, m), 8.51-8.57 (2H, m).

후처리

  1. concentrationThe reaction solvent was concentrated in vacuo
  2. dissolutionthe residue was dissolved in methanol
  3. additionTo the solution was added 1M sodium hydroxide solution (0.5 ml)
  4. stirringstirred for 30 minutes
  5. customThe solution was evaporated
  6. custompartitioned between chloroform and water
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by preparative thin-layer chromatography on silica gel (ethyl acetate)

출처 및 근거

ORD 기록
ord-c1ad96e04b3246eb98c77917de8485a0
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008229

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