3-Hydroxybutanoic acid, (R)- → (2R)-4-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol

HRID 1876570

반응식

HRID 1876570 반응식
[OH:1][C@H:2]([CH3:7])[CH2:3][C:4]([OH:6])=O.O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:38]1([C:44]2[N:52]=[C:51]([C:53]3[CH:54]=[N:55][C:56]([NH2:59])=[N:57][CH:58]=3)[N:50]=[C:49]3[C:45]=2[N:46]=[C:47]([N:65]2[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]2)[N:48]3[CH2:60][C:61]([F:64])([F:63])[F:62])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>C(N(CC)CC)C.CN(C)C=O>[NH2:59][C:56]1[N:57]=[CH:58][C:53]([C:51]2[N:50]=[C:49]3[C:45]([N:46]=[C:47]([N:65]4[CH2:70][CH2:69][N:68]([C:4](=[O:6])[CH2:3][C@H:2]([OH:1])[CH3:7])[CH2:67][CH2:66]4)[N:48]3[CH2:60][C:61]([F:62])([F:64])[F:63])=[C:44]([N:38]3[CH2:39][CH2:40][O:41][CH2:42][CH2:43]3)[N:52]=2)=[CH:54][N:55]=1

참가 물질

7

반응물 4

HCID 921353-Hydroxybutanoic acid, (R)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866419965-[6-Morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetateHCID 178526939HCID 178526939, 화합물

생성물 1

HCID 59333595(2R)-4-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol수율 48.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

(R)-3-hydroxybutanoic acid (39 mg, 0.38 mmol), hydroxybenzotriazole hydrate (58 mg, 0.38 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (72 mg, 0.38 mmol), dimethylformamide (5 ml), triethylamine (161 μl) were added to 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate (200 mg, 0.29 mmol) and the resulting mixture was stirred for 15 hours. The reaction mixture was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=19:1) to give the title compound (77 mg, 48%) as a colorless solid.

후처리

  1. customThe reaction mixture was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (chloroform:methanol=19:1)

출처 및 근거

ORD 기록
ord-e6abb0760c7d4bf58b849e12d88c9d55
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309546B2

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