Formaldehyde → HCID 23654287, 화합물

HRID 597934노트

반응식

HRID 597934 반응식
[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

참가 물질

7

반응물 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 23654286HCID 23654286, 화합물

생성물 1

HCID 23654287HCID 23654287, 화합물수율 86%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3696943225d48f48ebd929422354e46
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897595B2

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