N,N-Diethyl-2,3-dimethylbenzamide → HCID 58863415, compound

HRID 1159558Notes

Reaction equation

HRID 1159558 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([CH2:7][CH2:8][CH2:9][C:10]#[N:11])[C@@H:4]([CH2:12][OH:13])[CH2:3]1.C(N(CC)[C:17](=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[CH3:25])C>>[OH:1][C@H:2]1[CH2:6][N:5]([CH2:7][CH2:8][CH2:9][C:10]2[NH:11][C:17](=[O:26])[C:18]3[C:19]([CH:25]=2)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[C@@H:4]([CH2:12][OH:13])[CH2:3]1

Participants

3

Reactant 2

HCID 15621069N,N-Diethyl-2,3-dimethylbenzamideHCID 68644191HCID 68644191, compound

Product 1

HCID 58863415HCID 58863415, compound

Procedure

(3R,5R)-5-Hydroxymethylpyrrolidin-3-ol and 4-bromobutyronitrile are reacted in the presence of potassium carbonate in N,N-dimethylformamide to give 4-[(2R,4R)-4-hydroxy-2-hydroxymethylpyrrolidin-1-yl]butyronitrile. In the same manner as in Example 1b (e) and using 4-[(2R,4R)-4-hydroxy-2-hydroxymethylpyrrolidin-1-yl]butyronitrile and N,N-diethyl-2,3-dimethylbenzamide, 3-{3-[(2R,4R)-4-hydroxy-2-hydroxymethylpyrrolidin-1-yl]propyl}-5-methyl-2H-isoquinolin-1-one is obtained.

Sources & evidence

ORD record
ord-c05a136f1d7e48b3823baa73778ec4a7
Source dataset
uspto-grants-2010_10
Patent number
US07812178B2

Reaction notes

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