(R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone → HCID 178521030, compound

HRID 931309Notes

Reaction equation

HRID 931309 reaction equation
[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10](=[NH:14])OCC)[CH2:9][CH2:8]2)[CH:6]=1.N[C:16]1[C:21]([NH2:22])=[CH:20][N:19]=[C:18]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH2:24]2)[N:17]=1>C(O)(=O)C>[F:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10]3[NH:14][C:20]4[C:21]([N:22]=3)=[CH:16][N:17]=[C:18]([N:23]3[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)=[O:30])[CH2:24]3)[N:19]=4)[CH2:8][CH2:9]2)[CH:6]=1

Participants

4

Reactant 2

HCID 89853288(R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanoneHCID 117966480Ethyl 1-(4-fluoro-1H-pyrazol-1-yl)cyclopropanecarbimidate

Product 1

HCID 178521030HCID 178521030, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 1-(4-fluoro-1H-pyrazol-1-yl)cyclopropanecarbimidate (148 mg, 0.75 mmol) and acetic acid (0.8 mL) were added to the filtrate containing (R)-(1-(4,5-diaminopyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone, prepared in the previous step. The reaction mixture was heated at reflux for 16 h. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 0-4% methanol in ethyl acetate) to afford the title compound. MS (ES+APCI) (M+H) 425.2; LCMS retention time: 3.545 min (Method V1).

Workup

  1. customprepared in the previous step
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 16 h
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 0-4% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-fb3e36fccc874f27924e6cf72a5f279d
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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