Diisopropylethylamine → HCID 9821924, 화합물

HRID 896056

반응식

HRID 896056 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][CH:7]=[C:6]2[CH2:13][C:14](O)=O.CCN(C(C)C)C(C)C.[NH2:26][C:27]1[C:28](=[O:40])[N:29]([CH3:39])[C:30](=[O:38])[N:31]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:32]=1[NH2:33]>C(#N)C>[CH2:34]([N:31]1[C:32]2[N:33]=[C:14]([CH2:13][C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:9]=[N:8][CH:7]=3)[NH:26][C:27]=2[C:28](=[O:40])[N:29]([CH3:39])[C:30]1=[O:38])[CH:35]([CH3:37])[CH3:36]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 41103394,5-Diamino-3-isobutyl-1-methylpyrimidine-2,6-dioneHCID 22226532(6-Methoxy-isoquinolin-4-yl)-acetic acid

생성물 1

HCID 9821924HCID 9821924, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of (6-methoxy-isoquinolin4-yl)-acetic acid (3.5 g, 13.82 mmol) in acetonitrile (70 ml) is treated sequentially with Hunig's base (6.15 ml, 36 mmol), O-(7-benzotriazo-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (6.29 g, 16.6 mmol) and 5,6-diamino-1-isobutyl-3-methyl-1H-pyrimidine-2,4-dione (3.22 g, 15.2 at mmol) while the solution is stirred at room temperature. The reaction is stirred at ambient temperature for 2 h, prior to evaporation of the solvent. The residue is tritruated with ethyl acetate (50 ml) filtered and washed with ethyl acetate and then dried at 50° C. under reduced pressure. The resulting intermediate is suspended in a mixture of methanol (30 ml) and 4M aqueous sodium hydroxide (60 ml) and heated at 80° C. for 45 minutes. This suspension is neutralized with acetic acid and cooled to 0-5° C. overnight. The resultant solid is collected by filtration, and washed with methanol/water 1:9 (30 ml) followed by methanol (30 ml). Drying under high vacuum at 50° C. affords 3-isobutyl-8-(6-methoxy-isoquinolin-4-ylmethyl)-1-methyl-3,7-dihydro-purine-2,6-dione, [MH]+ 394.5.

후처리

  1. stirringThe reaction is stirred at ambient temperature for 2 h
  2. customto evaporation of the solvent
  3. filtrationfiltered
  4. washwashed with ethyl acetate
  5. customdried at 50° C. under reduced pressure
  6. additionThe resulting intermediate is suspended in a mixture of methanol (30 ml) and 4M aqueous sodium hydroxide (60 ml)
  7. temperatureheated at 80° C. for 45 minutes
  8. temperaturecooled to 0-5° C. overnight
  9. filtrationThe resultant solid is collected by filtration
  10. washwashed with methanol/water 1:9 (30 ml)
  11. customDrying under high vacuum at 50° C.

출처 및 근거

ORD 기록
ord-6774e6ac959c4ec79778227db821f929
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919337B2

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