Hydroxylamine → 5-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]benzaldehydeoxime

HRID 734814Notes

Reaction equation

HRID 734814 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH:30]([CH3:33])[CH2:29][CH2:28]4)=[C:20]([CH:23]=3)[CH:21]=O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[NH2:34][OH:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][C:19]([O:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][CH:30]([CH3:33])[CH2:31][CH2:32]4)=[C:20]([CH:23]=3)[CH:21]=[N:34][OH:35])=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 787HydroxylamineHCID 86601135HCID 86601135, compound

Product 1

HCID 729841845-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]benzaldehydeoxime

Procedure

The product was obtained analogously to Example 14.1d starting from 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]benzaldehyde (Example 14.1c) and hydroxylamine. Yield: 40 mg (46% of theoretical); C28H28ClN3O2 (M=473.994); calc.: molpeak (M+H)+: 474/476 (Cl); found: molpeak (M+H)+: 474/476 (Cl); HPLC-MS: 5.68 minutes (method A).

Workup

  1. customThe product was obtained analogously to Example 14.1d
  2. custom5.68 minutes (method A)

Sources & evidence

ORD record
ord-ebc5bff40cb3472ea4478754608e7e73
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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