Diisopropylethylamine → HCID 59536344, compound
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[N:30]1[O:31][N:32]=[C:33]2[CH:38]=[C:37]([C:39](Cl)=[O:40])[CH:36]=[CH:35][C:34]=12>C(Cl)Cl>[N:30]1[O:31][N:32]=[C:33]2[CH:38]=[C:37]([C:39]([N:10]3[CH2:11][CH2:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[C@H:9]3[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=3)=[O:40])[CH:36]=[CH:35][C:34]=12Participants
Procedure
To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (50 mg, 180 μmol) and diea (31 μL, 180 μmol) in DCM (1 mL) was added benzo[c][1,2,5]oxadiazole-5-carbonyl chloride (43 mg, 234 μmol). The resulting mixture was then stirred at RT for overnight. Then, the mixture was concentrated and the residue was dissolved in MeOH (1 mL). The solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA) to give a desired product, which was then dissolved in MeOH (1 mL). The solution was then washed through PL-HCO3 resin and the resin was then washed with MeOH (1 mL). The combined washings were concentrated and dried under vacuum to give the title compound as a white solid. MS (ESI, positive ion) m/z: 424 (M+H).
Workup
- concentrationThen, the mixture was concentrated
- dissolutionthe residue was dissolved in MeOH (1 mL)
- customThe solution mixture was then purified by preparative HPLC (0%-100% MeCN 0.1% TFA/H2O 0.1% TFA)
Sources & evidence
- ORD record
- ord-d24eb78a06da4cceb7ac0674cc2d2a0b
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476297B2
Reaction notes
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