Hydrochloric Acid → 7-Amino-2-chloro-8-(2-hydroxy-2-methylpropyl)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide

HRID 871876노트

반응식

HRID 871876 반응식
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[Cl:9][C:10]1[N:15]=[C:14]([NH:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[C:13]([C:22](F)=[O:23])=[CH:12][N:11]=1.Cl>CN(C=O)C.O>[NH2:2][C:1]1[N:16]([CH2:17][C:18]([OH:21])([CH3:19])[CH3:20])[C:14]2[N:15]=[C:10]([Cl:9])[N:11]=[CH:12][C:13]=2[C:22](=[O:23])[C:3]=1[C:4]([NH2:6])=[O:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydride2회HCID 891066152-Chloro-4-(2-hydroxy-2-methylpropylamino)pyrimidine-5-carboxylic acid fluoride

생성물 1

HCID 866731447-Amino-2-chloro-8-(2-hydroxy-2-methylpropyl)-5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide수율 57%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
3.5 °C

실험 절차

To a solution, cooled to 2-5°C. on an ice bath, of 4.4 g (52.36 mmol) of cyanoacetamide in 70 mL of anhydrous DMF are added portionwise 4.19 g (104.72 mmol) of 60% sodium hydride. The mixture is stirred for 15 minutes at 2-5°C., and this suspension is then added rapidly to a solution of 12.35 g (49.87 mmol) of the acid fluoride prepared in step 17.2 in 70 mL of anhydrous DMF, precooled to 2-5°C. The mixture is stirred overnight at room temperature and is then cooled to 2-5°C. on an ice bath, and 2.09 g (52.36 mmol) of 60% sodium hydride are added portionwise. The reaction mixture is stirred for 3 hours at room temperature and then poured into a mixture of ice, 100 mL of water and 150 mL of aqueous 1N HCl. The yellow precipitate formed is isolated by filtration, rinsed with water and then dried in an oven. After triturating in methanol and drying in an oven, 8.84 g of the expected product are finally obtained in the form of a yellow solid. Yield=57%.

후처리

  1. customprecooled to 2-5°C
  2. stirringThe mixture is stirred overnight at room temperature
  3. temperatureis then cooled to 2-5°C. on an ice bath
  4. stirringThe reaction mixture is stirred for 3 hours at room temperature
  5. customThe yellow precipitate formed
  6. customis isolated by filtration
  7. washrinsed with water
  8. customdried in an oven
  9. customAfter triturating in methanol
  10. customdrying in an oven

출처 및 근거

ORD 기록
ord-a10dbece4fff41dd9f3981cb5045a1e7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975250B2

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