Tetrahydrofuran → HCID 44180311, compound
Reaction equation
ClC[C:3]1[CH:4]=[C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][CH2:29][C:30]4[C:31]([NH:43][CH:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)=[C:32]5[CH:40]=[N:39][N:38]([CH2:41][CH3:42])[C:33]5=[N:34][C:35]=4[CH2:36][CH3:37])=[O:27])[CH:21]=3)=[O:19])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:50][N:51]([CH3:56])[CH2:52][CH2:53][NH:54][CH3:55].[CH2:57]1COCC1>>[CH2:41]([N:38]1[C:33]2=[N:34][C:35]([CH2:36][CH3:37])=[C:30]([CH2:29][NH:28][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([C:18]([NH:17][CH2:16][C:11]4[CH:10]=[C:9]([C:5]5[CH:4]=[CH:3][CH:8]=[C:7]([CH2:50][N:51]([CH2:52][CH2:53][N:54]([CH3:57])[CH3:55])[CH3:56])[CH:6]=5)[C:14]([F:15])=[CH:13][CH:12]=4)=[O:19])[CH:21]=3)=[O:27])[C:31]([NH:43][CH:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[C:32]2[CH:40]=[N:39]1)[CH3:42]Participants
4
Procedure
N-{[3′-(Chloromethyl)-6-fluoro-3-biphenylyl]methyl}-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide (0.034 g, 0.05 mmol) and N,N,N′-trimethyl-1,2-ethanediamine (0.025 g, 0.25 mmol) were combined in THF (1 mL) and microwaved at 150° C. for 1 h. Purification on a Gilson HPLC using a TFA system was followed by passing the product though a quaternary ammonium hydroxide cartridge to give the free base, the title compound, as a white solid. LC-MS m/z 748.8 (M+H)+, 1.43 min (ret time); mp 126-129° C. Analytical HPLC shows 99.1% purity, (ret time 9.788 min).
Workup
- custommicrowaved at 150° C. for 1 h
- customPurification on a Gilson HPLC
- customto give the free base
Sources & evidence
- ORD record
- ord-874d6ec55be146efbbd74236274b8184
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067408B2
Reaction notes
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