Morpholine → HCID 10203141, compound

HRID 897278Notes

Reaction equation

HRID 897278 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.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[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:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:11]=1)=[O:13]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 10271271HCID 10271271, compound

Product 1

HCID 10203141HCID 10203141, compound

Procedure

A solution of the chloride from Example 44 Step 5 (14 mg, 0.037 mmol) in morpholine (0.5 ml) was heated at 120C 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 (0.5 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 (0.5 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-10fb9ef733994490b0a94f6a46c70478
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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