Trifluoroacetic acid → HCID 86624994, compound
Reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].Cl[C:9]1[N:10]=[C:11]([NH:33][C:34]2[CH:39]=[CH:38][N:37]=[CH:36][N:35]=2)[C:12]2[N:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[N:16]=[C:15]([CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[C:13]=2[N:14]=1.[CH3:40][C@@H:41]1[CH2:46][NH:45][CH2:44][CH2:43][NH:42]1.C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CS(C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:40][C@H:41]1[NH:42][CH2:43][CH2:44][N:45]([C:9]2[N:10]=[C:11]([NH:33][C:34]3[CH:39]=[CH:38][N:37]=[CH:36][N:35]=3)[C:12]3[N:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]([F:25])([F:23])[F:24])[N:16]=[C:15]([CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[C:13]=3[N:14]=2)[CH2:46]1Participants
Conditions
- Temperature
- 110 °C
Procedure
5-Chloro-3-(morpholin-4-ylmethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidin-7-amine trifluoroacetate (150 mg, 0.2 mmol), (R)(−)-2-methylpiperazine (86 mg, 0.85 mmol) and N,N-diisopropylethylamine (140 mg, 1.0 mmol) were mixed in methyl sulfoxide (1.0 ml) in a reaction vial. The reaction mixture was heated at 110° C. for 18 hours. The reaction was cooled to room temperature and brought to acidic condition by adding trifluoroacetic acid. The crude reaction mixture was purified on reverse phase HPLC (5-95% acetonitrile in water with 0.05% trifluoroacetic acid) and lyophilized to give 5-[(3R)-3-methylpiperazin-1-yl]-3-(morpholin-4-ylmethyl)-N-pyrimidin-4-yl-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidin-7-amine trifluoroacetate (143 mg).
Workup
- temperatureThe reaction was cooled to room temperature
- customThe crude reaction mixture
- customwas purified on reverse phase HPLC (5-95% acetonitrile in water with 0.05% trifluoroacetic acid)
Sources & evidence
- ORD record
- ord-3d696a3ba53941e5b3564de1e1827b96
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569572B2
Reaction notes
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