1-(4-Aminopiperidin-1-yl)ethan-1-one → HCID 10092678, compound

HRID 1371638Notes

Reaction equation

HRID 1371638 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[F:19])=[O:9])=[CH:6][N:5]=[C:4](S(CC)(=O)=O)[N:3]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]1>C(O)(C)C>[NH2:1][C:2]1[C:7]([C:8](=[O:9])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[C:11]=2[F:19])=[CH:6][N:5]=[C:4]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]2)[N:3]=1

Participants

4

Reactant 2

HCID 49624771-(4-Aminopiperidin-1-yl)ethan-1-oneHCID 21070569HCID 21070569, compound

Product 1

HCID 10092678HCID 10092678, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of (4-amino-2-ethanesulfonyl-pyrimidin-5-yl)-(2,6-difluoro-3-methoxy-phenyl)-methanone (20.0 mg, 0.056 mmol, Example 89) and 1-(4-amino-piperidin-1-yl)-ethanone (21.1 mg, 0.148 mmol, prepared as described in U.S. Pat. No. 5,817,828) in isopropyl alcohol (2.5 mL) was heated at 120° C. in a sealed tube under microwave conditions for 0.3 to 1 hour. The resulting reaction mixture was evaporated in vacuo and crude product was purified on silica gel with 95:5 of dichloromethane/methanol to give 1-[4-[4-amino-5-(2,6-difluoro-3-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidin-1-yl]-ethanone as a white solid (18.3 mg). MS (M+H)+, 406.

Workup

  1. customprepared
  2. customThe resulting reaction mixture
  3. customwas evaporated in vacuo and crude product
  4. customwas purified on silica gel with 95:5 of dichloromethane/methanol

Sources & evidence

ORD record
ord-57863aa65fc44ebf91e831be68e81080
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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