Formaldehyde → HCID 23654287、化合物

HRID 597934ノート

反応式

HRID 597934 の反応式
[BH3-][C:2]#[N:3].[Na+].[CH3:5][O:6][C:7]1[C:8](N)=[CH:9][C:10]2[CH:16]([CH3:17])[CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:13][CH2:12][C:11]=2[N:24]=1.C=O.[C:28]([O-])([O-])=O.[K+].[K+]>CC#N.CC(O)=O>[CH3:5][O:6][C:7]1[C:8]([N:3]([CH3:2])[CH3:28])=[CH:9][C:10]2[CH:16]([CH3:17])[CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:13][CH2:12][C:11]=2[N:24]=1

参加物

7

反応物 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 23654286HCID 23654286、化合物

生成物 1

HCID 23654287HCID 23654287、化合物収率 86%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6342Acetonitrile溶媒

実験手順

NaBH3CN (63.0 mg, 990 μmol) was added portionwise at room temperature to a solution of 2-methoxy-5-methyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-3-amine (100 mg, 330 μmol) and HCHO (37% in H2O, 2.31 mmol) in MeCN (1 ml). The mixture was stirred at room temperature for 15 min before slow addition of HOAc (0.2 ml). The reaction was stirred at room temperature for an additional 3 h and was basified with aq. K2CO3 and extracted with DCM. The organic layer was washed with water, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to provide 94.0 mg (86%) of 2-methoxy-N,N,5-trimethyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-3-amine. MS (ESI) m/z 332. 2-Methoxy-N,N,5-trimethyl-7-(trifluoroacetyl)-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-3-amine (35.0 mg, 106 μmol) was treated under basic condition (K2CO3/MeOH/H2O), as described above, to provide 17 mg (68%) of 2-methoxy-N,N,5-trimethyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepin-3-amine. MS (ESI) m/z 236.

後処理

  1. extractionextracted with DCM
  2. washThe organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-e3696943225d48f48ebd929422354e46
出典データセット
uspto-grants-2011_03
特許番号
US07897595B2

反応ノート

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