Water → 4-Methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbonitrile

HRID 1876751노트

반응식

HRID 1876751 반응식
CCOC(C)=O.O.[C:8]([C:10]1[C:11]([CH3:30])=[N:12][C:13]([N:16]([CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)C(=O)C)=[N:14][CH:15]=1)#[N:9]>Cl>[CH3:30][C:11]1[C:10]([C:8]#[N:9])=[CH:15][N:14]=[C:13]([NH:16][CH2:20][CH2:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[N:12]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 68527494N-(5-cyano-4-methyl-pyrimidin-2-yl)-N-[3-(1-methyl-piperidin-4-yl)-propyl]-acetamide

생성물 1

HCID 445457774-Methyl-2-[3-(1-methyl-piperidin-4-yl)-propylamino]-pyrimidine-5-carbonitrile

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

The resultant mixture was treated at 20-25° C. with a dilute HCl solution (37% HCl (4.80 g) diluted with water (15.00 g)), followed by EtOAc (9.02 g) and water (10.00 g). The resultant mixture was settled and the top organic layer was removed. The acidic aqueous layer was stirred at room temperature for 1 h to yield a mixture (which contained the hydrolysis product, N-(5-cyano-4-methyl-pyrimidin-2-yl)-N-[3-(1-methyl-piperidin-4-yl)-propyl]-acetamide). The aqueous layer was extracted one time with EtOAc (9.02 g). 2-Methyl-THF (8.60 g) was added and the pH of the biphasic mixture was adjusted to about pH=12 by addition of 6N NaOH (9.69 g). The aqueous layer was removed and the 2-Me-THF layer was diluted with 2-MeT-HF (8.60 g) and dried with MgSO4 (1.0 g). The pH of the dried 2-MeTHF solution was adjusted to about pH=1 by dropwise addition of 5-6N HCl/IPA, whereupon the HCl salt of the title compound precipitated. The solid was filtered, dissolved in EtOH (3.95 g) and the pH was adjusted to about pH=12 using 6N NaOH (4.85 g). The solid which precipitated during the addition was filtered, washed with water (10.00 g) and dried in a vacuum oven at 60-70° C. for 5 h to yield the title compound as a solid.

후처리

  1. customthe top organic layer was removed
  2. customto yield a mixture (which
  3. extractionThe aqueous layer was extracted one time with EtOAc (9.02 g)
  4. addition2-Methyl-THF (8.60 g) was added
  5. additionthe pH of the biphasic mixture was adjusted to about pH=12 by addition of 6N NaOH (9.69 g)
  6. customThe aqueous layer was removed
  7. additionthe 2-Me-THF layer was diluted with 2-MeT-HF (8.60 g)
  8. dry with materialdried with MgSO4 (1.0 g)
  9. additionThe pH of the dried 2-MeTHF solution was adjusted to about pH=1 by dropwise addition of 5-6N HCl/IPA, whereupon the HCl salt of the title compound
  10. customprecipitated
  11. filtrationThe solid was filtered
  12. dissolutiondissolved in EtOH (3.95 g)
  13. customThe solid which precipitated during the addition
  14. filtrationwas filtered
  15. washwashed with water (10.00 g)
  16. customdried in a vacuum oven at 60-70° C. for 5 h

출처 및 근거

ORD 기록
ord-ea6b73b317514df0bc78a0dd0e072aac
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309720B2

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