Hydrochloric Acid → HCID 18353676、化合物

HRID 430074ノート

反応式

HRID 430074 の反応式
C(O[CH:4](OCC)[CH2:5][CH2:6][NH:7][C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)C.Cl.CC([O-])=O.[Na+].[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]2[CH2:40][CH2:39][NH:38]2)[CH:33]=[CH:34][C:35]=1[Cl:36].C([BH3-])#N.[Na+]>C1COCC1>[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]2[CH2:40][CH2:39][N:38]2[CH2:4][CH2:5][CH2:6][NH:7][C:8]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:33]=[CH:34][C:35]=1[Cl:36]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 183536582-[3,3-Diethoxypropylamino]-4-methoxyquinolineHCID 18353681HCID 18353681、化合物

生成物 1

HCID 18353676HCID 18353676、化合物収率 80.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-[3,3-Diethoxypropylamino]-4-methoxyquinoline (0.046 g, 0.15 mmol) in THF (4 ml) was treated with 0.5M HCl (2 ml) for 10 min. The reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml) was added NaOAc (0.024 g, 0.3 mmol), 2-(3,4-dichlorophenyl)azetidine (0.03 g) and sodium cyanoborohydride (0.009 g, 0.15 mmol). After reaction for 40 min at 20° C., the reaction was evaporated to dryness under reduced pressure, and the residue partitioned between ethyl acetate and sat. sodium bicarbonate. The organic layer was dried, evaporated to dryness under reduced pressure and purified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (50 mg, 80%); δH (CD3OD) 1.55 (2H, m), 2.0 (1H, m), 2.25 (1H, m), 2.45-2.7 (2H, m), 2.8 (1H, m), 3.2-3.4 (4H, m), 3.9 (3H, s), 3.95 (1H, t), 6.0 (1H, s), 7.05 (1H, t), 7.15-7.5 (5H, m), 7.8 (1H, d); MS (ES+) 416/418 (47/32%, MH+), 244 (50), 201 (100).

後処理

  1. customThe reaction mixture was evaporated to dryness and to the residue in methanol/HOAc (1 ml/0.018 ml)
  2. customAfter reaction for 40 min at 20° C.
  3. customthe reaction was evaporated to dryness under reduced pressure
  4. customthe residue partitioned between ethyl acetate and sat. sodium bicarbonate
  5. customThe organic layer was dried
  6. customevaporated to dryness under reduced pressure
  7. custompurified by chromatography on silica gel eluting with 1-3% (9:1 MeOH/NH3) in dichloromethane

出典と根拠

ORDレコード
ord-a3078d8c9b1840909e6517502c166810
出典データセット
uspto-grants-2001_11
特許番号
US06320051B1

反応ノート

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