Pyridine → HCID 86622010, compound

HRID 1029055Notes

Reaction equation

HRID 1029055 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C@H:5]([N:8]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[N:31]([C:32]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:30]=[N:29][N:28]=2)=[CH:17][CH:16]=1)[C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH:6]=O.N1C=CC=CC=1>O>[OH:3][N:2]=[CH:4][C@@H:5]([N:8]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[N:31]([C:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[N:30]=[N:29][N:28]=2)=[CH:19][CH:20]=1)[C:9](=[O:13])[CH2:10][CH2:11][CH3:12])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 86622009HCID 86622009, compound

Product 1

HCID 86622010HCID 86622010, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Hydroxylamine hydrochloride (25.4 mg, 0.4 mmol) was added to a solution of intermediate (5c) (174 mg, 0.3 mmol), pyridine (3 mL, 37 mmol) and water (1.5 mL, 83 mmol) at room temperature. After 15 minutes, water (10 mL) was added and the mixture was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with saturated aqueous NaCl (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography gave intermediate (5d) as a white solid (148 mg).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×20 mL)
  2. washThe combined organic extracts were washed with saturated aqueous NaCl (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8232d70005294711a52f5bf85af452b4
Source dataset
uspto-grants-2014_05
Patent number
US08735625B2

Reaction notes

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