Cyclopentylamine → HCID 10189495, compound

HRID 2229201Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH2:10]Br)=[C:6]([O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:14]([N:16]([CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]2[C:31]=1[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15].[CH:41]1([NH2:46])[CH2:45][CH2:44][CH2:43][CH2:42]1>CN1CCCC1=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][NH:46][CH:41]2[CH2:45][CH2:44][CH2:43][CH2:42]2)=[C:6]([O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:14]([N:16]([CH2:22][C:23]1[N:24]=[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]2[C:31]=1[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[O:39][CH3:40])[CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To 0.1 ml of a 0.2 M solution of (2-chloro-3-bromoethoxy-4-methoxyphenyl)-N-({3-[(2-methoxyphenyl)methyl](imidazolo[1,2-a]pyridin-2-yl)}methyl)-N-(3-methylbutyl)carboxamide in N-methylpyrrolidinone is added 0.1 ml of a 1 M solution of cyclopentylamine. The mixture is heated at 90 ° C. for 15 h in a sealed vial. After cooling to room temperature, the reaction mixture is diluted with 0.5 ml of ethyl acetate and washed with 0.5 ml of 1 N aqueous sodium hydroxide. The organic layer is separated and purified by preparative TLC eluting with 9/1/0.5 ethyl acetate/methanol/triethylamine to obtain 11 mg of the title compound. Mass Spec m/z (M++1) 633.

Workup

temperatureAfter cooling to room temperature
washwashed with 0.5 ml of 1 N aqueous sodium hydroxide
customThe organic layer is separated
custompurified by preparative TLC
washeluting with 9/1/0.5 ethyl acetate/methanol/triethylamine

Sources & evidence

ORD record: ord-40eb598dbe594484bc5fdab1b0fdc367
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420365B1

Reaction notes

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