Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 57608090, compound

HRID 2426370Notes

Reaction equation

HRID 2426370 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].Cl.O(N)C.[NH2:10][C:11]1[C:20]2[N:21]=[C:22]([CH2:30]Cl)[N:23]([CH2:24][C:25]3([OH:29])[CH2:28][CH2:27][CH2:26]3)[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1.Cl.ClCC1N(CC(C)C)C2C(C)=C(C)N=C(N)C=2N=1>>[NH2:10][C:11]1[C:20]2[N:21]=[C:22]([CH2:30][N:3]([O:4][CH3:5])[CH3:2])[N:23]([CH2:24][C:25]3([OH:29])[CH2:28][CH2:27][CH2:26]3)[C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=1

Participants

5

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 521874O-Methylhydroxylamine hydrochlorideHCID 575155221-{[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanolHCID 67262971HCID 67262971, compound

Product 1

HCID 57608090HCID 57608090, compound

Procedure

1-[(4-Amino-2-{[methoxy(methyl)amino]methyl}-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanol was prepared according to the general methods of Part I of Example 9 using N,O-dimethyl hydroxylamine hydrochloride in lieu of methoxylamine hydrochloride and using 1-{[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclobutanol in lieu of 2-(chloromethyl)-1-isobutyl-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride. The crude product was purified by HPFC eluting with a gradient of 0-35% CMA in chloroform and then recrystallized from acetonitrile to provide pure product as a white powder, mp 219.0-221.0° C. Anal. Calcd for C18H23N5O2 C, 63.32; H, 6.79; N, 20.51. Found: C, 63.12; H, 6.56; N, 20.16.

Workup

  1. customThe crude product was purified by HPFC
  2. washeluting with a gradient of 0-35% CMA in chloroform
  3. customrecrystallized from acetonitrile
  4. customto provide pure product as a white powder, mp 219.0-221.0° C

Sources & evidence

ORD record
ord-cd25fff9842f4aca960e041d39ea1190
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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