Ethyl orthoformate → HCID 21984054, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:9][CH:8]=[C:7]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:6]=2.[NH2:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([C:35]=1[NH:36][CH2:37][C:38]([CH3:41])([OH:40])[CH3:39])=[CH:33][C:32]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[CH:31][CH:30]=2.[CH:49](OCC)(OCC)OCC>>[CH2:18]([C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[CH:26]=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.[CH2:42]([C:32]1[CH:31]=[CH:30][C:29]2[N:28]=[CH:27][C:26]3[N:25]=[CH:49][N:36]([CH2:37][C:38]([CH3:41])([OH:40])[CH3:39])[C:35]=3[C:34]=2[CH:33]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1Participants
5
Procedure
For Examples 431 and 434, a modification of the method described in Part B of Examples 427–429 was used to treat 1-(3-amino-7-benzylquinolin-4-ylamino)-2-methylpropan-2-ol or 1-(3-amino-6-benzylquinolin-4-ylamino)-2-methylpropan-2-ol with triethyl orthoformate, as indicated in the table below. The reaction was heated at reflux for one hour and then stirred overnight at ambient temperature. A precipitate formed, which was isolated by filtration to provide 1-(7-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol or 1-(8-benzyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.
Workup
- temperatureThe reaction was heated
- temperatureat reflux for one hour
- customA precipitate formed
- customwhich was isolated by filtration
Sources & evidence
- ORD record
- ord-7c4ba5b0737a4f89b2ca5ce53f1a44b3
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091214B2
Reaction notes
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