Dichloromethane → 8-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(4-pyridylacetamido)pyridin-3-yl]acryloylglycyl]amino]-benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

HRID 365570노트

반응식

HRID 365570 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([NH:12][CH2:13][C:14]([N:16]([C:18]2[C:19]([Cl:46])=[C:20]([C:42]([Cl:45])=[CH:43][CH:44]=2)[CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[C:27]3[C:32]=2[N:31]=[C:30]([CH3:33])[CH:29]=[C:28]3[O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)[CH3:17])=[O:15])=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.ClCCl.Cl.[N:58]1[CH:63]=[CH:62][C:61]([CH2:64][C:65](Cl)=[O:66])=[CH:60][CH:59]=1>O>[Cl:46][C:19]1[C:18]([N:16]([CH3:17])[C:14](=[O:15])[CH2:13][NH:12][C:10](=[O:11])/[CH:9]=[CH:8]/[C:5]2[CH:6]=[N:7][C:2]([NH:1][C:65](=[O:66])[CH2:64][C:61]3[CH:62]=[CH:63][N:58]=[CH:59][CH:60]=3)=[CH:3][CH:4]=2)=[CH:44][CH:43]=[C:42]([Cl:45])[C:20]=1[CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[C:30]([CH3:33])[CH:29]=[C:28]2[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 232920204-Pyridineacetyl chloride hydrochlorideHCID 232920288-[3-[N-[(E)-3-(6-aminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

생성물 1

HCID 113202628-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(4-pyridylacetamido)pyridin-3-yl]acryloylglycyl]amino]-benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline수율 9.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 8-[3-[N-[(E)-3-(6-aminopyridin-3-yl)acryloylglycyl]-N-methylamino]-2,6-dichlorobenzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (90 mg), triethylamine (56 mg) and dichloromethane (2 ml) was added 4-pyridylacetyl chloride hydrochloride (53 mg) in ice water bath under nitrogen atmosphere, and the mixture was stirred for 1 hour at the same temperature and allowed to stand for 1 day at ambient temperature. The reaction mixture was poured into water and extracted with chloroform. 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 (chloroform:methanol=10:1, V/V) to give 8-[2,6-dichloro-3-[N-methyl-N-[(E)-3-[6-(4-pyridylacetamido)pyridin-3-yl]acryloylglycyl]amino]-benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (10 mg) as an amorphous powder.

후처리

  1. waitto stand for 1 day at ambient temperature
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

출처 및 근거

ORD 기록
ord-548575f98ce747e1a3726e854d0aebab
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127389

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