Potassium Carbonate → benzyl 4-((R)-2-((6-chloro-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate

HRID 2080303Notes

Reaction equation

Cl[C:2]1[N:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:28])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:5].[Cl-].Cl.[O:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH:37]1[CH2:42][CH2:43][NH2:44].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:33][C:31]1[CH:30]=[CH:29][C:3]([C:4]([NH:6][CH2:7][C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13](=[O:28])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:5])=[C:2]([NH:44][CH2:43][CH2:42][CH:37]2[CH2:38][CH2:39][CH2:40][CH2:41][O:36]2)[N:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of chloride (R)-benzyl 4-(2-((2,6-dichloronicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (150 mg, 0.304 mmol), 2-(tetrahydro-2H-pyran-2-yl)ethanamine HCl salt (76 mg, 0.459 mmol), K2CO3 (125 mg, 0.905 mmol) and DMF (1 mL) was stirred at 100° C. for 10 hrs. The crude mixture was purified on RP-HPLC using a mixture of acetonitrile and H2O to give benzyl 4-((R)-2-((6-chloro-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (62 mg, 35%). LRMS (M+H+) m/z 586.3.

Workup

customThe crude mixture was purified on RP-HPLC
additiona mixture of acetonitrile and H2O

Sources & evidence

ORD record: ord-2869ac6372614bb8a97d7327dece4dd3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932270B2

Reaction notes

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