Hydrochloric Acid → HCID 58188021, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[C:10]([C:18](O)=[O:19])[CH:9]=2)=[CH:4][CH:3]=1.[Si]([O:28][CH2:29][C@H:30]([C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[NH2:31])(C(C)(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl>CN(C)C=O.CO>[OH:28][CH2:29][C@@H:30]([NH:31][C:18]([C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=1)=[O:19])[C:32]1[CH:33]=[N:34][C:35]([CH3:38])=[CH:36][CH:37]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4′-methyl-5-(methylsulfonyl)biphenyl-3-carboxylic acid (37 mg, 0.12 mmol) in N,N-dimethylformamide (1 mL) were added (S)-2-(tert-butyldimethylsilyloxy)-1-(6-methylpyridin-3-yl)ethanamine (80 mg, 0.27 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (120 mg, 0.32 mmol) and N,N-diisopropylethylamine (120 μL, 0.69 mmol). The reaction mixture was stirred for 16 hours at 25° C. LC-MS indicated the reaction was complete. To the reaction mixture were added MeOH (2 mL) and 12N aq. HCl (0.5 mL). The mixture was stirred at rt for 2 hrs and then concentrated in vacuo. The residue was purified by preparative HPLC (100×21.2 mm C18 column, MeCN-water[10 mM Et2NH]) to afford the final product as a light color solid.
Workup
- stirringThe mixture was stirred at rt for 2 hrs
- concentrationconcentrated in vacuo
- customThe residue was purified by preparative HPLC (100×21.2 mm C18 column, MeCN-water[10 mM Et2NH])
Sources & evidence
- ORD record
- ord-1253dd4a59694d529498d0a17021d6d9
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946439B2
Reaction notes
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