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

HRID 1468847Notes

Reaction equation

HRID 1468847 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-04023ad106ce4cb2bddc82e33550ec37
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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