Acetic Acid → 5-ethyl-2-{4-[(1R,2R)-2-({[4-(1H-tetrazol-1-yl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}pyrimidine

HRID 1468847ノート

反応式

HRID 1468847 の反応式
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][O:19][CH2:20][C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+].[CH:32](OC)(OC)OC.C(O)(=O)C.C([O-])(O)=O.[Na+]>O>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([C@H:15]3[CH2:17][C@H:16]3[CH2:18][O:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([N:25]4[CH:32]=[N:30][N:29]=[N:28]4)=[CH:26][CH:27]=3)[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 867177934-[({(1R,2R)-2-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]cyclopropyl}methoxy)methyl]aniline

生成物 1

HCID 711352745-ethyl-2-{4-[(1R,2R)-2-({[4-(1H-tetrazol-1-yl)benzyl]oxy}methyl)cyclopropyl]piperidin-1-yl}pyrimidine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

The product of step A (60 mg, 0.16 mmol), sodium azide (13 mg, 0.2 mmol), trimethyl orthoformate (0.3 mL, 2.7 mmol), and acetic acid (0.15 mL, 2.6 mmol) were heated at 80° C. for 6 hours. The solution was cooled and diluted with water. The solution was neutralized with NaHCO3 and extracted with DCM. The organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified via reverse-phase HPLC (C18: gradient 10-100 water/acetonitrile 0.1% formic acid) which yielded the title compound. MS (ESI) m/z 420 [M+H]+. GPR119 Human EC50: 0.07 nM

後処理

  1. temperatureThe solution was cooled
  2. extractionextracted with DCM
  3. dry with materialThe organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified via reverse-phase HPLC (C18: gradient 10-100 water/acetonitrile 0.1% formic acid) which

出典と根拠

ORDレコード
ord-04023ad106ce4cb2bddc82e33550ec37
出典データセット
uspto-grants-2015_04
特許番号
US09006228B2

反応ノート

読み込み中…