Hydroxylamine → HCID 59835828, compound

HRID 1916654Notes

Reaction equation

HRID 1916654 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-a28f385ba9924ed6bdc738c811f4c52f
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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