Ethoxyacetyl chloride → 8-benzyloxy-2-ethoxymethyl-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.[CH2:55]([O:57][CH2:58][C:59](Cl)=O)[CH3:56]>>[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:29]([CH2:28][O:35][CH2:36][CH3:45])=[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:56]([CH2:55][O:57][CH2:58][CH3:59])[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 228 and 230, 7-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (Example 228) or 6-benzyloxy-N4-(tetrahydro-2H-pyran-4-ylmethyl)quinoline-3,4-diamine (Example 230) can be treated with ethoxyacetyl chloride according to the method described in Part C of Example 50 to provide 7-benzyloxy-2-ethoxymethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (Example 228) or 8-benzyloxy-2-ethoxymethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (Example 230).
Sources & evidence
- ORD record
- ord-15b50765638d4470a65927a94e818d10
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897597B2
Reaction notes
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