3-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile → 4-{4-tert.-Butoxycarbonylamino-3-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert.-butyl ester

HRID 1635280Notes

Reaction equation

HRID 1635280 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:16]([NH2:28])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)[O:35][C:34]([C:36]2[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=2)[C:39]#[N:40])=[CH:33][C:32](=O)[O:31]1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:16]([NH:28][C:32](=[O:31])[CH2:33][C:34]([C:36]3[CH:43]=[CH:42][CH:41]=[C:38]([C:39]#[N:40])[CH:37]=3)=[O:35])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 117363373-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrileHCID 695928501(2h)-Pyridinecarboxylic acid,4-[3-amino-4-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-3,6-dihydro-,1,1-dimethylethyl ester

Product 1

HCID 865880134-{4-tert.-Butoxycarbonylamino-3-[3-(3-cyano-phenyl)-3-oxo-propionylamino]-phenyl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert.-butyl esterYield 92%

Procedure

Prepared from 4-(3-amino-4-tert.-butoxycarbonylamino-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert.-butyl ester (Example G29) (544 mg, 1.4 mmol) and 3-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile (Example J4) (336 mg, 1.5 mmol) according to the general procedure K. Obtained as an orange solid (722 mg).

Sources & evidence

ORD record
ord-c5b98631ea874c58aeda5c991f3a7a8e
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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