Dimethylformamide → HCID 57505880, 화합물

HRID 1514184노트

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HRID 1514184 반응식
FC(F)(F)S(O[C:7]1[C:17]2[CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=O)=O.[CH3:27][N:28](C=O)C>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[C:27]([C:7]1[C:17]2[CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)#[N:28]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 575058791,1-Dimethylethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

생성물 1

HCID 57505880HCID 57505880, 화합물

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 8857Ethyl Acetate용매

실험 절차

1,1-dimethylethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 13) (5 g), zinc (II) cyanide (1.5 g) and tetrakis(triphenylphoshine)palladium(0) (1.5 g) were heated in dry DMF at 150° C. for 18 hours. The cooled reaction mixture was diluted with EtOAc (200 ml) and filtered. The filtrate was washed with saturated sodium bicarbonate, (200 ml), water (200 ml) and brine (200 ml). The crude reaction mixture was dried in the usual manner and evaporated. Purification by chromatography (eluting with DCM) yielded the title compound (3.4 g). δH (400 MHz, CDCl3) 7.50 (1H, d), 7.35 (1H, d), 7.27-7.21 (1H), m), 3.62-3.56 (4H, m), 3.22-3.20 (2H, m), 2.97-2.94 (2H, m), 1.47 (9H, s); MS (ES) C16H20N2O2 requires 272; found 217 [M+H−56]+, 273 [M+H]+.

후처리

  1. customThe cooled reaction mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated sodium bicarbonate, (200 ml), water (200 ml) and brine (200 ml)
  4. customThe crude reaction mixture
  5. customwas dried in the usual manner
  6. customevaporated
  7. customPurification
  8. washby chromatography (eluting with DCM)

출처 및 근거

ORD 기록
ord-11ba4179c9754318a3e961c3225d7c8f
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222245B2

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