Triethylamine → 4-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile

HRID 1161542노트

반응식

HRID 1161542 반응식
[NH:1]([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].C(N(CC)CC)C.C[O:17][C:18](=O)[N:19]=[C:20](SC)[C:21]([C:31]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[C:33]([O:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:32]=1[F:50])=[N:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=1.[B-]C#N.[Na+]>C1COCC1.C(OCC)(=O)C.C(O)(=O)C.CO>[Si:43]([O:42][CH2:41][CH2:40][O:39][C:33]1[C:32]([F:50])=[C:31]([CH:21]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[C:20]2[NH:19][C:18](=[O:17])[N:1]([C:3]3[N:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[N:2]=2)[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=1)([C:46]([CH3:48])([CH3:49])[CH3:47])([CH3:45])[CH3:44]

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 3465582-HydrazinylpyrimidineHCID 20587905Sodium cyanoborohydride [MI]HCID 72312754(2-{3-[2-(t-Butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester

생성물 1

HCID 1359820434-[({3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl)amino]benzonitrile수율 105.5%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

After adding 600 mg of 2-hydrazinopyrimidine and 1.5 ml of triethylamine to a solution of 3.2 g of (2-{3-[2-(t-butyldimethylsilanyloxy)ethoxy]-2-fluoro-5-methoxyphenyl}-2-(4-cyanophenylimino)-1-methylsulfanylethylidene)carbamic acid methyl ester in 30 ml of THF, the mixture was stirred overnight at 60° C. under a nitrogen atmosphere. Next, 30 ml of methanol and 4.5 ml of acetic acid were added to the reaction mixture. After then adding 3 g of sodium cyanotrihydroborate to the solution, the mixture was stirred at room temperature for 5 hours. Ethyl acetate was added to the reaction mixture. After washing the organic layer with water and saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure to give the title compound (3.4 g, crude product) as a light yellow solid.

후처리

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. washAfter washing the organic layer with water and saturated brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6f1d0c81ee324a37ab7528d714169484
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816522B2

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