Hydroxylamine → HCID 59835828, compound

HRID 271691Notes

Reaction equation

HRID 271691 reaction equation
[NH2:1][OH:2].C(N(CC)CC)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:25]3[CH:26]=[CH:27][C:28]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[C:29]([CH:32]=3)[CH:30]=O)=[N:21][CH:22]=2)=[CH:13][CH:12]=1.C(#N)C>O.C([O-])(O)=O.[Na+].CO>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:25]3[CH:26]=[CH:27][C:28]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[C:29]([CH:32]=3)[CH:30]=[N:1][OH:2])=[N:21][CH:22]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 787HydroxylamineHCID 6342AcetonitrileHCID 8471TriethylamineHCID 59835895HCID 59835895, compound

Product 1

HCID 59835828HCID 59835828, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
85 °C

Procedure

27 mg (0.38 mmol) hydroxylamine and 53 μL (0.38 mmol) triethylamine are added to a solution of 200 mg (0.35 mmol) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-benzaldehyde (Example 3.55b) in 2 mL of a 1:1 mixture of acetonitrile and MeOH. The reaction solution is heated to 85° C. After the reaction is complete the mixture is diluted with water and saturated NaHCO3 solution and the organic phase is extracted with DCM. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography using HPLC-MS.

Workup

  1. extractionthe organic phase is extracted with DCM
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe purification

Sources & evidence

ORD record
ord-82ea6a468f0f4d07b1ad7465b6dc8a82
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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