Pyrrolidine → 2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)-6-(pyrrolidin-1-yl)nicotinamide

HRID 547367Notes

Reaction equation

Cl[C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:7])=[C:4]([NH:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[N:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>CO>[F:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][CH2:19][NH:18][C:4]1[N:3]=[C:2]([N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH:17]=[CH:16][C:5]=1[C:6]([NH:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:7]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 6-chloro-2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)nicotinamide (50 mg, 0.13 mmol) and pyrrolidine (94 mg, 1.3 mmol) in a sealed tube was heated to 150° C. for 10 min. LC/MS indicated the reaction was complete. The crude was diluted with MeOH, filtered, and purified on RP-HPLC using a mixture of acetonitrile and H2O to a give 2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)-6-(pyrrolidin-1-yl)nicotinamide (20.2 mg, 37%). LRMS (M+H+) m/z 420.2.

Workup

filtrationfiltered
custompurified on RP-HPLC
additiona mixture of acetonitrile and H2O to a give 2-(3-fluorophenethylamino)-N-(pyridin-3-ylmethyl)-6-(pyrrolidin-1-yl)nicotinamide (20.2 mg, 37%)

Sources & evidence

ORD record: ord-a5e8cf9ffb184397a113f46919162bb0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939534B2

Reaction notes

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