Acetic Acid → 1-Methyl-1H-pyrazole-3-sulfonic acid (2-acetyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-benzyl-amide
Reaction equation
[CH2:1]([N:8]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][NH:23][CH2:22][CH2:21]2)[S:9]([C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28](O)(=[O:30])[CH3:29].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C(#N)C>[C:28]([N:23]1[CH2:22][CH2:21][C:20]2[C:25](=[CH:26][CH:27]=[C:18]([N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[S:9]([C:12]3[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=3)(=[O:11])=[O:10])[CH:19]=2)[CH2:24]1)(=[O:30])[CH3:29]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-methyl-1H-pyrazole-3-sulfonic acid benzyl-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide (24 mg, 0.06 mmol) and acetic acid (3.6 μl, 0.06 mmol) in dry acetonitrile (2 ml) was added 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (24 mg, 0.06 mmol), then diisopropylethylamine (33 μl, 0.20 mmol) and the solution was stirred at 50° C. for 16 hrs. The reaction mixture was concentrated in vacuo and the residue purified using preparative HPLC to afford the title compound as a white solid (17 mg, 67% yield), HPLC retention time 3.97 min. Mass spectrum (ES+) m/z 425 (M+H).
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- customthe residue purified
Sources & evidence
- ORD record
- ord-6f680b55119e49a48588dba6e7f2463b
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426442B2
Reaction notes
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