Hydroxyamine hydrochloride → HCID 136335752, compound

HRID 2233941Notes

Reaction equation

HRID 2233941 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[C:20]([Cl:26])[N:19]=2)[CH2:14][CH2:13]1)=[O:10].Cl.[NH2:28][OH:29]>CO>[NH2:25][C:24](=[N:28][OH:29])[C:22]1[CH:21]=[C:20]([Cl:26])[N:19]=[C:18]([N:15]2[CH2:14][CH2:13][CH:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[CH2:17][CH2:16]2)[CH:23]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86608292HCID 86608292, compound

Product 1

HCID 136335752HCID 136335752, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4-Dichloro-N-[1-(6-chloro-4-cyanopyridin-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide (Example 95; 150 mg, 0.362 mmol) was dissolved in MeOH (5 ml) and TEA (100 μl, 0.724 mmol) was added. Hydroxylamine hydrochloride (25.2 mg, 0.362 mmol) was added and the mixture was refluxed for 1 h. The solvent was removed in vacuo and the resulting precipitate was dissolved in DMSO and purified by semi preparative reverse phase HPLC eluting with CH3CN/H2O (0.1% TFA). (80 mg).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting precipitate was dissolved in DMSO
  4. custompurified by semi preparative reverse phase HPLC
  5. washeluting with CH3CN/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-a79ed01317ba41c1a208e02bc1062618
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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