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Water → Taprizosin

HRID 1795392
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HRID 1795392 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:5]([O:16][CH3:17])=[C:4]([O:18][CH3:19])[CH:3]=1.[C:20]([N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][C:28]=2[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]1)#[N:21].O.C(OC(C)C)(=O)C>CS(C)=O.C(#N)C>[NH2:9][C:8]1[C:7]2[C:2](=[CH:3][C:4]([O:18][CH3:19])=[C:5]([O:16][CH3:17])[C:6]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:1]=[C:20]([N:22]2[CH2:31][CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][C:28]=3[NH:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:23]2)[N:21]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 7915Isopropyl AcetateHCID 9856336N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamideHCID 99430356-Amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile

생성물 1

HCID 6433102Taprizosin수율 87.6%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of 6-amino-3,4-dimethoxy-2-(2-pyridyl)benzonitrile (see Example 2 or 2A, 50 g, 196 mmol) and N-(2-cyano-1,2,3,4-tetrahydro-5-isoquinolyl)methanesulfonamide (see Example 3 or 3A, 63 g, 251 mmol) in DMSO (300 ml) at room temperature, was added sodium-t-pentoxide (64.2 g, 582 mmol) portionwise over 120 minutes keeping the temperature below 30° C. The resulting slurry was then stirred for 2 hours. After this time, water (500 ml) was added over 5 minutes followed by isopropyl acetate (150 ml). The aqueous phase was collected and partitioned with ethyl acetate (500 ml) before reducing the pH of the biphasic mixture to a range of 7.0–8.0 with 12M aqueous HCl (22 ml). The aqueous phase was extracted with ethyl acetate (250 ml). The combined organics were reduced in volume and replaced with acetonitrile to give a final volume of 500 ml and stirred for 13 hours. After this time, the resulting slurry was filtered to yield 105 g of the crude product. This was then suspended in acetonitrile (525 ml), heated to reflux for one hour, cooled to room temperature and stirred for 13 hours. The resulting slurry was filtered to yield 87 g (87%) of the title compound.

후처리

  1. customthe temperature below 30° C
  2. customThe aqueous phase was collected
  3. custompartitioned with ethyl acetate (500 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate (250 ml)
  5. customto give a final volume of 500 ml
  6. stirringstirred for 13 hours
  7. filtrationAfter this time, the resulting slurry was filtered
  8. customto yield 105 g of the crude product
  9. temperatureheated
  10. temperatureto reflux for one hour
  11. stirringstirred for 13 hours
  12. filtrationThe resulting slurry was filtered

출처 및 근거

ORD 기록
ord-6864c97019ea438f85cbd911d2b3f340
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07026479B2

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