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Triethylamine → 6-({2-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamino}methyl)-4H-benzo[1,4]thiazin-3-one

HRID 1435872
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HRID 1435872 반응식
Cl.[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.[O:30]=[C:31]1[NH:36][C:35]2[CH:37]=[C:38]([CH:41]=O)[CH:39]=[CH:40][C:34]=2[S:33][CH2:32]1.[BH4-].[Na+]>C(Cl)Cl.CCO>[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][CH2:41][C:38]2[CH:39]=[CH:40][C:34]3[S:33][CH2:32][C:31](=[O:30])[NH:36][C:35]=3[CH:37]=2)=[CH:16][CH:15]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 684436432-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt

생성물 1

HCID 99119256-({2-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamino}methyl)-4H-benzo[1,4]thiazin-3-one수율 69%

시약·촉매·용매

2
HCID 702Ethanol용매2회HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 2-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt (1.76 mmole) in dry CH2Cl2 (25 mL) and dry EtOH (10 mL) at RT was added triethylamine (0.74 mL, 5.28 mmole) and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxaldehyde (0.34 g, 1.76 mmole). After 24 h, the reaction contents were concentrated and dried under high vacuum. To a stirred solution of the crude imine in dry EtOH (25 mL) at RT was added NaBH4 (0.66 g, 1.76 mmole). After 24 h, the reaction solution was concentrated under vacuum and to the residue was added 1M HCl (5 mL) and EtOAc (50 mL): After stirring for 1 h, 6M NaOH (1 mL) was added and the organic layer was separated, dried (Na2SO4) and concentrated. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.55 g, 69%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.11 (d, J=4.5 Hz, 1H), 8.57 (d, J=9.1 Hz, 1H), 8.27 (d, J=4.5 Hz, 1H), 8.14 (m, 2H), 7.90 (s, 2H), 7.61 (m, 3H), 7.46 (d, J=7.1 Hz, 1H), 7.22 (m, 2H), 5.52 (m, 2H), 4.23 (s, 2H), 4.08 (s, 3H), 3.68 (s, 2H), 3.19 (m, 2H). LC-MS (ES) m/e 457 (M+H)+.

후처리

  1. customthe reaction contents
  2. concentrationwere concentrated
  3. customdried under high vacuum
  4. waitAfter 24 h
  5. concentrationthe reaction solution was concentrated under vacuum and to the residue
  6. additionwas added 1M HCl (5 mL) and EtOAc (50 mL)
  7. addition6M NaOH (1 mL) was added
  8. customthe organic layer was separated
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customPurification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

출처 및 근거

ORD 기록
ord-77aefa69b5164b918b8d9f5f8f4fff94
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618959B2

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