Trifluoroacetic acid → HCID 59594561, compound

HRID 2262674Notes

Reaction equation

HRID 2262674 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[CH3:10][CH2:11][C:12](=O)[CH2:13][CH3:14].C(O)(C(F)(F)F)=O>C(OC(C)=O)(C)C>[Cl:9][C:5]1[CH:6]=[C:7]([NH:8][CH:12]([CH2:13][CH3:14])[CH2:11][CH3:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7288Ethyl ketoneHCID 12682545-Chloropyridine-2,3-diamine

Product 1

HCID 59594561HCID 59594561, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

To a solution of 2,3-diamino-5-chloropyridine (7.0 g, 48.6 mmol, 1.0 equiv) and 3-pentanone (6.16 mL, 58.3 mmol, 1.2 equiv) in iPrOAc (100 mL) was added TFA (7.2 mL, 97.2 mmol, 2.0 equiv) by syringe. After stirring for 10 min, NaHB(OAc)3 (20 g, 97.2 mmol, 2.0 equiv) was added as a solid in several portions over ˜5 min. The reaction was allowed to stir overnight. The reaction mixture was then washed with satd. aq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC (10%-40% EtOAc/Hexanes) provided 5-chloro-N3-(pentan-3-yl)pyridine-2,3-diamine as a beige solid (2.6 g, 25%). m/z=214.1 [M+H]+

Workup

  1. stirringto stir overnight
  2. washThe reaction mixture was then washed with satd
  3. dry with materialaq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel MPLC (10%-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-4ce7b64c968c45f990c1644bce7b8dc7
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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