Cyclopentylamine → (2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl)cyclopentylamine

HRID 734897Notes

Reaction equation

HRID 734897 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:18][N:17]=2)=[CH:10][CH:9]=1)(=O)=O.[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:15]#[C:14][C:11]3[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][NH:34][CH:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:9][CH:10]=3)=[N:17][CH:18]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 866011402-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl methanesulfonate

Product 1

HCID 57845301(2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl)cyclopentylamine

Procedure

The product was prepared analogously to Example 1.1g from 60 mg (0.15 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenyl}ethyl methanesulfonate and 0.03 mL (0.30 mmol) of cyclopentylamine (6 hours at 50° C., potassium carbonate as base). Yield: 20 mg (34% of theoretical); C26H25ClN2 (M=400.943); calc.: molpeak (M+H)+:401/403 (Cl); found: molpeak (M+H)+:401/403 (Cl); HPLC-MS: 5.0 minutes (method H).

Workup

  1. custom5.0 minutes (method H)

Sources & evidence

ORD record
ord-dac738d126e34f0c9a8428a5a640a0cc
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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