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Sodium cyanoborohydride → 1-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-[3-{2-[bis-(2-pyridin-3-yl-ethyl)-amino]ethyl}-2-(3,5-dimethyl-phenyl)-1H-indol-5-yl]-2-methylpropan-1-one

HRID 1274388
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HRID 1274388 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]=O)[CH:2]=1.[NH2:10][CH2:11][CH2:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:22]([CH3:33])([CH3:32])[C:23]([N:25]3[CH:29]4[CH2:30][CH2:31][CH:26]3[CH2:27][CH2:28]4)=[O:24])[CH:20]=2)[NH:15][C:14]=1[C:34]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=1.[C:42]([BH3-])#[N:43].[Na+]>CO.C(O)(=O)C>[CH:26]12[N:25]([C:23](=[O:24])[C:22]([C:19]3[CH:20]=[C:21]4[C:16](=[CH:17][CH:18]=3)[NH:15][C:14]([C:34]3[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=3)=[C:13]4[CH2:12][CH2:11][N:10]([CH2:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH2:8][CH2:7][C:3]3[CH:2]=[N:43][CH:42]=[CH:5][CH:4]=3)([CH3:33])[CH3:32])[CH:29]([CH2:28][CH2:27]1)[CH2:30][CH2:31]2
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참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 11073404Pyridin-3-ylacetaldehydeHCID 117617912-[3-(2-Aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one

생성물 1

HCID 99174031-(7-Aza-bicyclo[2.2.1]hept-7-yl)-2-[3-{2-[bis-(2-pyridin-3-yl-ethyl)-amino]ethyl}-2-(3,5-dimethyl-phenyl)-1H-indol-5-yl]-2-methylpropan-1-one

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
2회
HCID 887Methanol용매

실험 절차

To a solution of pyridin-3-yl-acetaldehyde (120 mg in a mixture of 5 mL methanol and 0.018 mL glacial acetic acid) was added 141 mg of 2-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-aza-bicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one followed by 20 mg 3Å powdered molecular seives. To this mixture, 68 mg sodium cyanoborohydride was added and the pH adjusted to 5.5 by the addition of 10% methanolic acetic acid. After 15.5 hours, the reaction was quenched by the addition of saturated sodium bicarbonate and the mixture extracted with ethyl acetate. The organic portion was washed successively with saturated ammonium chloride, sodium bicarbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 92:8) gave the title compound (130 mg). MASS: 640 (M+H)

후처리

  1. customthe reaction was quenched by the addition of saturated sodium bicarbonate
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe organic portion was washed successively with saturated ammonium chloride, sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. customPurification of the
  6. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 92:8)

출처 및 근거

ORD 기록
ord-1268b9d86c5244aa9d6ce97156807bae
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06156767

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