HCID 10271271, compound → HCID 10159819, compound

HRID 897276Notes

Reaction equation

HRID 897276 reaction equation
Cl[C:2]1[N:11]=[C:10]([C:12]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)=[O:13])[C:9]([OH:24])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2>N1CCCCC1>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][NH:14][C:12]([C:10]1[C:9]([OH:24])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([N:7]2[CH2:8][CH2:3][CH2:4][CH2:5][CH2:6]2)[N:11]=1)=[O:13]

Participants

3

Reactant 1

HCID 10271271HCID 10271271, compound

Product 1

HCID 10159819HCID 10159819, compound

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution of the chloride from Example 44 Step 5 (40 mg, 0.105 mmol) in piperidine (0.5 ml) was heated at 100 C. for 36 hrs under argon. The resulting solution was cooled to room temperature and the solvent evaporated in vacuo. The residue was dissolved in hot DMF (0.7 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionThe residue was dissolved in hot DMF (0.7 ml)
  3. custompurified by preparative HPLC
  4. wash(Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50×20 mm I.D., C18, S-5 um, 120A) eluting with 5-95% acetonitrile/water (0.1% TFA) at 15 ml/min)

Sources & evidence

ORD record
ord-5d0f73d4b2fa472597043e284f359665
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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