Acetic Acid → HCID 178521022, compound

HRID 931321Notes

Reaction equation

HRID 931321 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:16])[CH2:10]2)=[N:6][C:7]=1[NH2:8].[N:22]1[N:23]([C:27]2([C:30](=N)OCC)[CH2:29][CH2:28]2)[N:24]=[CH:25][CH:26]=1.C(N(CC)CC)C.C(O)(=O)C>C(O)C>[N:22]1[N:23]([C:27]2([C:30]3[NH:8][C:7]4=[N:6][C:5]([N:9]5[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:17]6[CH2:21][CH2:20][CH2:19][CH2:18]6)=[O:16])[CH2:10]5)=[CH:4][CH:3]=[C:2]4[N:1]=3)[CH2:29][CH2:28]2)[N:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 89853725Ethyl 1-(2H-1,2,3-triazol-2-yl)cyclopropanecarbimidateHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 178521022HCID 178521022, compoundYield 2.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (0.4 g, 1.36 mmol) in ethanol was added ethyl 1-(2H-1,2,3-triazol-2-yl)cyclopropanecarbimidate (600 mg, crude), triethylamine (5 mL) and acetic acid (6 mL). The reaction mixture was heated to reflux for 12 h. The solvent was evaporated and the residue was dissolved in ethyl acetate. The solution was dried over sodium sulfate and concentrated. The crude material was purified via preparative TLC to afford the title compound (16 mg). MS (ES+) (M+H) 407.3; LCMS retention time 1.793 min (Method N1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude material was purified via preparative TLC

Sources & evidence

ORD record
ord-ca12328d062d4f4f968677f500abb534
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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