Ammonium Hydroxide → HCID 58869114, compound

HRID 1623121Notes

Reaction equation

[CH3:1][O:2][N:3]([CH:7]([CH3:27])[CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:13]=[C:12]1[CH2:24][CH2:25][CH3:26])[C:4](=[O:6])[CH3:5].CO[N:30](CCCCN1C2C3C=CC=CC=3N=CC=2N=C1CCC)C(=O)C.[OH-].[NH4+]>>[NH2:30][C:15]1[C:14]2[N:13]=[C:12]([CH2:24][CH2:25][CH3:26])[N:11]([CH2:10][CH2:9][CH2:8][CH:7]([N:3]([O:2][CH3:1])[C:4](=[O:6])[CH3:5])[CH3:27])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

Reactant 3

HCID 14923Ammonium Hydroxide

HCID 86612247HCID 86612247, compound

HCID 86612252HCID 86612252, compound

Product 1

HCID 58869114HCID 58869114, compound

Procedure

A modification to the general procedure of Part G of Example 6 was followed using N-methoxy-N-[1-methyl-4-(2-propyl-1H-imidazo-[4,5-c]quinolin-1-yl)butyl]-acetamide (1.0 g, 2.71 mmol) in lieu of N-methoxy-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide. The reaction mixture was cooled to 0° C. before addition of the ammonium hydroxide. Recrystallization from hot acetonitrile following flash column chromatography provided 0.059 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-1-methylbutyl]-N-methoxyacetamide as a tan crystalline solid, mp 140-142° C. MS (APCI) m/z 384.1 (M+H+); Theor. Mass: 384.240 Da Meas. Mass: 384.2406 Da. Mass Dev. 1.6 ppm.

Workup

customRecrystallization from hot acetonitrile following flash column chromatography

Sources & evidence

ORD record: ord-f75b39565ed0404c94e58698364d808a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

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