Ethyl orthopropionate → 8-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline
Reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:20][CH2:21][CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[C:14]([NH2:19])[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([O:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[CH:41][C:40]([NH2:46])=[C:39]2[NH:47][CH2:48][CH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:55](OCC)(OCC)(OCC)[CH2:56][CH3:57]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:20]([CH2:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[C:28]([CH2:29][CH3:30])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:28]([O:35][C:36]1[CH:45]=[CH:44][C:43]2[N:42]=[CH:41][C:40]3[N:46]=[C:55]([CH2:56][CH3:57])[N:47]([CH2:48][CH:49]4[CH2:54][CH2:53][O:52][CH2:51][CH2:50]4)[C:39]=3[C:38]=2[CH:37]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1Participants
5
Reactant 3
Product 2
Procedure
For examples 229 and 231, 7-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (Example 229) or 6-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (Example 231) can be treated with triethyl orthopropionate according to the general method described in Part G of Example 1 to provide 7-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (Example 229) or 8-benzyloxy-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (Example 231).
Sources & evidence
- ORD record
- ord-acc74599e43740048c75a765b211f4b4
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897597B2
Reaction notes
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