Triethylamine → 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide

HRID 227026노트

반응식

HRID 227026 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20]([OH:22])=O)=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>O.C(#N)C>[CH3:27][O:26][N:25]([CH3:24])[C:20]([C:11]1[C:12](=[O:19])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]([CH2:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=2)[CH:10]=1)=[O:22]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 111923Propylphosphonic anhydrideHCID 577547691-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

생성물 1

HCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide수율 90.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

9.45 g (26.3 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 2.82 g (28.9 mmol) of N,O-dimethylhydroxylamine hydrochloride, 22 mL (16 g, 158 mmol) of triethylamine and 18.8 mL (20.1 g, 31.6 mmol) of 50% 1-propanephosphonic acid cyclic anhydride were sequentially added to 250 mL acetonitrile at rt. After 1 h 400 mL of water were added and the mixture was extracted two times with 300 mL DCM. Combined organic layers were evaporated and the residue purified on silica flash column using 0-15% methanol in EtOAc to give 9.62 g of the product as an off-white solid.

후처리

  1. extractionthe mixture was extracted two times with 300 mL DCM
  2. customCombined organic layers were evaporated
  3. customthe residue purified on silica flash column

출처 및 근거

ORD 기록
ord-9545d53462e94db7a3fe24c4105ca0f1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557213B2

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