O-Methylhydroxylamine hydrochloride → HCID 72448488, compound

HRID 1623193Notes

Reaction equation

HRID 1623193 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:23][CH2:24][CH3:25])[N:14]([CH2:15][C:16]([CH3:22])([CH3:21])[CH2:17][C:18](=O)[CH3:19])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.Cl.[CH3:27][O:28][NH2:29]>>[CH3:27][O:28][N:29]=[C:18]([CH2:17][C:16]([CH3:22])([CH3:21])[CH2:15][N:14]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=[C:13]1[CH2:23][CH2:24][CH3:25])[CH3:19]

Participants

3

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 58837347HCID 58837347, compound

Product 1

HCID 72448488HCID 72448488, compound

Procedure

By the general method of Part F in Example 30, 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-4,4-dimethylpentan-2-one was reacted with O-methylhydroxylamine hydrochloride to provide 5-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-4,4-dimethylpentan-2-one O-methyloxime as about a 49 to 1 mixture of E and Z isomers as a yellow solid after recrystallization from aqueous methanol, mp 196-198° C. MS (APCI) m/z 368 (M+H)+; Anal. calcd for C21H29N5O: C, 68.63; H, 7.95; N, 19.06. Found: C, 68.69; H, 7.66; N, 19.04.

Sources & evidence

ORD record
ord-90a7c6b48b534f2a87fcdcae78b063ca
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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