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

反応式

HRID 1876567 の反応式
[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

参加物

7

反応物 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、化合物

生成物 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-oxoethanol収率 78.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1b70cad33e4f48fbac966bbd9c322c82
出典データセット
uspto-grants-2012_11
特許番号
US08309546B2

関連ノート

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