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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
ノート
印刷プレビュー

反応式

HRID 1435872 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒

2
HCID 702Ethanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-77aefa69b5164b918b8d9f5f8f4fff94
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07618959B2

反応ノート

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