Acetic Acid → HCID 178521013, compound

HRID 931237Notes

Reaction equation

HRID 931237 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].[CH:22]1([C:26]2[N:31]=[C:30]([CH:32]=O)[CH:29]=[CH:28][N:27]=2)[CH2:25][CH2:24][CH2:23]1.[S].C(O)(=O)C>C(O)C>[CH:22]1([C:26]2[N:31]=[C:30]([C:32]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)[CH:29]=[CH:28][N:27]=2)[CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5362487SulfurHCID 649856792-Cyclobutylpyrimidine-4-carbaldehydeHCID 89854052(R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 178521013HCID 178521013, compound

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 (135.9 mg, 0.5 mmol) in ethanol was added 2-cyclobutylpyrimidine-4-carbaldehyde (76.2 mg, 0.5 mmol), sulfur (30.1 mg, 0.9 mmol) and acetic acid (0.15 mL) at room temperature under nitrogen. The reaction mixture was stirred for 16 h at reflux. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound as a yellow solid. MS (ES+APCI) (M+H) 432.1; LCMS retention time 2.567 min (Method G).

Workup

  1. temperatureat reflux
  2. customThe solvent was removed under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via preparative TLC

Sources & evidence

ORD record
ord-e5a365fc58404be792b4892bdb9cae95
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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