HCID 69507074, compound → HCID 69507151, compound

HRID 1623136Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[C:11]4[N:19]([CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[C:18]([CH2:26][CH2:27][CH3:28])=[N:17][C:12]=4[CH:13]=[N:14][C:15]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[N:31](CCCCN1C2C3C=CC=CC=3N=CC=2N=C1CCC)C(=O)C>>[NH2:31][C:13]1[C:12]2[N:17]=[C:18]([CH2:26][CH2:27][CH3:28])[N:19]([CH2:20][CH2:21][CH2:22][C:23](=[O:25])[CH3:24])[C:11]=2[C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:16][C:15]=2[N:14]=1

Participants

Reactant 2

HCID 69507074HCID 69507074, compound

HCID 86612247HCID 86612247, compound

Product 1

HCID 69507151HCID 69507151, compound

Procedure

The general method described in Part G of Example 6 was followed using 5-(7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (1.0 g, 2.69 mmol) in lieu of N-methoxy-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]acetamide. Recrystallization from hot methanol and water afforded 0.1815 g of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one as a tan powder, mp 202-204° C. MS (APCI) m/z 387.1 (M+H+); Anal. calcd for C24H26N4O 0.66H2O: C, 72.36; H, 6.91; N, 14.06. Found: C, 64.95; H, 7.78; N, 17.92.C24H26N4O 0.66H2O Exact Mass: Theor. Mass: 387.2185 Da. Meas. Mass: 387.2191 Da. Mass Dev. 1.5 ppm.

Workup

customRecrystallization from hot methanol and water

Sources & evidence

ORD record: ord-d9ec785be65840089069371dfa2e1068
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

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