1-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-ol → 1-(2-{4-[5-(2,4-Dichlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

HRID 734885Notes

Reaction equation

HRID 734885 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[N:13][C:12]([C:15]#[CH:16])=[CH:11][N:10]=1.I[C:18]1[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([CH3:32])([OH:31])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[CH:11][C:12]([C:15]#[C:16][C:18]2[CH:34]=[CH:33][C:21]([O:22][CH2:23][CH2:24][N:25]3[CH2:26][CH2:27][C:28]([CH3:32])([OH:31])[CH2:29][CH2:30]3)=[CH:20][CH:19]=2)=[N:13][CH:14]=1

Participants

3

Reactant 2

HCID 578453271-[2-(4-Iodophenoxy)ethyl]-4-methylpiperidin-4-olHCID 860769732-(2,4-Dichlorophenyl)-5-ethynylpyrazine

Product 1

HCID 578453131-(2-{4-[5-(2,4-Dichlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethyl)-4-methylpiperidin-4-ol

Procedure

The product was prepared analogously to Example 48.1c from 180 mg (0.72 mmol) of 2-(2,4-dichlorophenyl)-5-ethynylpyrazine and 260 mg (0.72 mmol) of 1-[2-(4-iodophenoxy)ethyl]-4-methylpiperidin-4-ol (IP 15) (stirring the reaction mixture overnight at RT). Yield: 16 mg (5% of theoretical); C26H25Cl2N3O2 (M=482.401); calc.: molpeak (M+H)+482/484/486 (2 Cl); found: molpeak (M+H)+:482/484/486 (2 Cl); HPLC-MS: 7.5 minutes (method G).

Workup

  1. custom7.5 minutes (method G)

Sources & evidence

ORD record
ord-d5ffd6d2e6f74c88b9622c323c419c7a
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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