Diisopropylcarbodiimide → HCID 59536414, 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.C(N=C=NC(C)C)(C)C.O.N1(O)C2C=CC=CC=2N=N1.[C:41]12([C:51](O)=[O:52])[CH2:50][CH:45]3[CH2:46][CH:47]([CH2:49][CH:43]([CH2:44]3)[CH2:42]1)[CH2:48]2>CN(C=O)C.CO>[C:41]12([C:51]([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:52])[CH2:48][CH:47]3[CH2:46][CH:45]([CH2:44][CH:43]([CH2:49]3)[CH2:42]1)[CH2:50]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.05 g, 0.2 mmol) in DMF (1 mL) was treated with N-((isopropylimino)methyl-ene)propan-2-amine (0.07 mL, 0.5 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (0.04 g, 0.2 mmol), and 1-adamantanecarboxylic acid (TCI, 0.04 g, 0.2 mmol). The resulting mixture was heated at 65° C. for 12 h. The reaction was cooled to RT and the filtrate was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)] to give the pure product. It was dissolved in methanol (10 mL) and neutralized by passing the solution through a Polymer Lab-HCO3 Macroporous resin cartridge, and the filtrate was concentrated to give (1R)-2-(tricyclo[3.3.1.1˜3,7˜]dec-1-ylcarbonyl)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline as a colorless solid. MS (ESI, positive ion) m/z: 440 (M+H).
Workup
- temperatureThe reaction was cooled to RT
- customthe filtrate was purified by preparative HPLC [gradient 10-90% MeCN (0.1% TFA)/H2O (0.1% TFA)]
- customto give the pure product
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-c2d98456e98b4da4adf16b357b2a25d0
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476297B2
Reaction notes
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