Triethylamine → HCID 58860789, compound
Reaction equation
CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:35][S:36]([C:39]1[CH:44]=[CH:43][C:42]([CH:45]([CH2:57][CH:58]2[CH2:63][CH2:62][O:61][CH2:60][CH2:59]2)[C:46]([NH:48][C:49]2[S:50][C:51]([C:54](O)=[O:55])=[CH:52][N:53]=2)=[O:47])=[CH:41][CH:40]=1)(=[O:38])=[O:37].Cl.[CH3:65][NH:66][O:67][CH3:68]>CN(C=O)C>[CH3:68][O:67][N:66]([CH3:65])[C:54]([C:51]1[S:50][C:49]([NH:48][C:46](=[O:47])[CH:45]([C:42]2[CH:41]=[CH:40][C:39]([S:36]([CH3:35])(=[O:38])=[O:37])=[CH:44][CH:43]=2)[CH2:57][CH:58]2[CH2:59][CH2:60][O:61][CH2:62][CH2:63]2)=[N:53][CH:52]=1)=[O:55]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
NEt3 (647 μL, 4.64 mmol) and BOP (976 mg, 2.21 mmol) were added to a stirred solution of 2-[2-(4-methanesulfonylphenyl)-3-(tetrahydropyran-4-yl)propionylamino]thiazole-5-carboxylic acid (EXAMPLE 127, 968 mg, 2.21 mmol) in anhydrous DMF (30 mL). After 5 min, N,O-dimethylhydroxylamine hydrochloride (237 mg, 2.43 mmol) was added, then the mixture was stirred at 20° C. for 18 h. The solvents were removed in vacuo, then the residue was dissolved in EtOAc (75 mL). The EtOAc solution was washed with saturated aqueous Na2CO3 (40 mL), 2M HCl (40 mL), and brine (40 mL), before being dried (MgSO4). Filtration and solvent evaporation provided the title compound: RTB=1.27 min; m/z (ES+)=482.0 [M+H]+.
Workup
- customThe solvents were removed in vacuo
- dissolutionthe residue was dissolved in EtOAc (75 mL)
- washThe EtOAc solution was washed with saturated aqueous Na2CO3 (40 mL), 2M HCl (40 mL), and brine (40 mL)
- dry with materialbefore being dried (MgSO4)
- filtrationFiltration and solvent evaporation
Sources & evidence
- ORD record
- ord-66a215f4ac544cb192d6ee9cccc4b1e7
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582632B2
Reaction notes
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