Glycolic Acid → 2-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanol

HRID 1876567

반응식

HRID 1876567 반응식
[OH:1][CH2:2][C:3]([OH:5])=O.O.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.FC(F)(F)C(O)=O.[N:36]1([C:42]2[N:50]=[C:49]([C:51]3[CH:52]=[N:53][C:54]([NH2:57])=[N:55][CH:56]=3)[N:48]=[C:47]3[C:43]=2[N:44]=[C:45]([N:63]2[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]2)[N:46]3[CH2:58][C:59]([F:62])([F:61])[F:60])[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(N(CC)CC)C.CN(C)C=O>[NH2:57][C:54]1[N:55]=[CH:56][C:51]([C:49]2[N:48]=[C:47]3[C:43]([N:44]=[C:45]([N:63]4[CH2:68][CH2:67][N:66]([C:3](=[O:5])[CH2:2][OH:1])[CH2:65][CH2:64]4)[N:46]3[CH2:58][C:59]([F:60])([F:62])[F:61])=[C:42]([N:36]3[CH2:37][CH2:38][O:39][CH2:40][CH2:41]3)[N:50]=2)=[CH:52][N:53]=1

참가 물질

7

반응물 4

HCID 757Glycolic AcidHCID 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 593335412-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-2-oxoethanol수율 78.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

2-Hydroxyacetic acid (15 mg, 0.19 mmol), hydroxybenzotriazole hydrate (37 mg, 0.19 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (37 mg, 0.19 mmol), dimethylformamide (3 ml), and triethylamine (100 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 (120 mg, 0.17 mmol) and the resulting mixture was stirred for 4 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was washed with saturated aqueous sodium bicarbonate solution and 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 (70 mg) as a colorless solid.

후처리

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

출처 및 근거

ORD 기록
ord-1b70cad33e4f48fbac966bbd9c322c82
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309546B2

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