2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → HCID 22349282, compound

HRID 896324Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:5]#[N:6].[C:15]([N:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]([CH2:27][C:28](O)=[O:29])[C:19]1=[O:31])([CH3:17])=[CH2:16].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C1COCC1>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([NH:10][CH2:11][CH2:12][CH2:13][OH:14])=[C:2]([NH:1][C:28](=[O:29])[CH2:27][N:20]2[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:18]([C:15]([CH3:17])=[CH2:16])[C:19]2=[O:31])[CH:3]=1)#[N:6]

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of 3-amino-4-(3-hydroxy-propylamino)-benzonitrile (484 mg, 2.53 mmol) and (3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetic acid (646 mg, 2.78 mmol) in THF (50 ml) was treated with EEDQ (625 mg, 2.53 mmol) and stirred for 48 h at 23° C. A grey precipitate was filtered off to give 526 mg (47%) of N-[5-Cyano-2-(3-hydroxy-propylamino)-phenyl]-2-(3-isopropenyl-2-oxo-2,3-dihydro-benzoimidazol-1-yl)-acetamide.

Workup

filtrationA grey precipitate was filtered off

Sources & evidence

ORD record: ord-da412dcc34d5478590cc2dd37dc19bed
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919331B2

Reaction notes

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