3'-Hydroxyphenylacetic acid → HCID 22172740, compound

HRID 47507

Reaction equation

HRID 47507 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[C:22]2[N:23]=[C:24]([CH2:29][CH2:30][CH2:31][CH3:32])[N:25]([CH2:26][CH2:27][NH2:28])[C:21]=2[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1>>[NH2:12][C:13]1[C:22]2[N:23]=[C:24]([CH2:29][CH2:30][CH2:31][CH3:32])[N:25]([CH2:26][CH2:27][NH:28][C:9](=[O:11])[CH2:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=3)[C:21]=2[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:14]=1

Participants

3

Reactant 2

HCID 121223'-Hydroxyphenylacetic acidHCID 219460272-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine

Product 1

HCID 22172740HCID 22172740, compoundYield 18.3%

Procedure

Using the general method of Example 97 3-hydroxyphenyl acetic acid (0.26 g, 1.7 mmole) was reacted with 2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethaneamine (0.5 g, 1.7 mmol) to provide 0.13 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-2-(3-hydroxyphenyl)acetamide as a white powder, m.p. 208-210° C. Analysis: Calculated for C23H26N6O2: %C, 66.01; %H, 6.26; %N, 20.08. Found: %C, 65.63; %H, 6.11; %N, 20.30. HRMS (EI) calcd for C23H26N6O2 (M+) 418.2117 found 418.2109.

Sources & evidence

ORD record
ord-727b474a416443038f6a045cd58c2656
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Linked notes

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