Sodium Bicarbonate → 4-(4-(2-Methyl-2-(6-(trifluoromethyl)-1H-indol-1-yl)propanoyl)-2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide
Reaction equation
[O:1]=[C:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1.[CH3:23][C:24]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]([F:41])([F:40])[F:39])[CH:36]=2)[CH:31]=[CH:30]1)([CH3:28])[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:28][C:24]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]([F:40])([F:41])[F:39])[CH:36]=2)[CH:31]=[CH:30]1)([CH3:23])[C:25]([N:6]1[CH2:5][CH2:4][N:3]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)(=[O:16])=[O:15])=[CH:12][CH:13]=2)[C:2](=[O:1])[CH2:7]1)=[O:26]Participants
6
Reactant 4
HCID 516892Sodium Bicarbonate
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 594656314-(2-Oxopiperazin-1-yl)-n-(thiazol-2-yl)benzenesulfonamide
HCID 594665612-Methyl-2-(6-(trifluoromethyl)-1h-indol-1-yl)propanoic acidProduct 1
Reagents, catalysts & solvents 1
Procedure
Synthesized according to general procedure 14, method B. The reaction was set up with 4-(2-oxopiperazin-1-yl)-N-(thiazol-2-yl)benzenesulfonamide (50 mg, 0.15 mmol), 2-methyl-2-(6-(trifluoromethyl)-1H-indol-1-yl)propanoic acid (27 mg, 0.10 mmol), HATU reagent (76 mg, 0.20 mmol), sodium bicarbonate (17 mg, 0.20 mmol), and DMF (0.20 mL) to obtain the desired amide as a white solid (50 mg, 0.10 mmol, 32% yield). LC/MS (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA), m/z: M+1 obs=592.4; tR=3.04 min.
Workup
- customSynthesized
Sources & evidence
- ORD record
- ord-27091c50ab8e48899161e6fa3294333e
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08586589B2
Reaction notes
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