Acetic Acid → HCID 10127135, compound
Reaction equation
C1C=CC2N(O)N=NC=2C=1.[C:11](O)(=[O:13])[CH3:12].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.FC(F)(F)C(O)=O.[NH2:42][CH2:43][CH2:44][N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48][CH:47]([NH:55][C:56]([C:58]2[NH:59][C:60]3[C:65]([CH:66]=2)=[CH:64][C:63]([Cl:67])=[CH:62][CH:61]=3)=[O:57])[C:46]1=[O:68]>C(Cl)Cl.C1COCC1.CCOC(C)=O>[CH3:46][CH2:47][CH2:48][CH:49]([CH3:54])[CH3:50].[C:11]([NH:42][CH2:43][CH2:44][N:45]1[C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48][CH:47]([NH:55][C:56]([C:58]2[NH:59][C:60]3[C:65]([CH:66]=2)=[CH:64][C:63]([Cl:67])=[CH:62][CH:61]=3)=[O:57])[C:46]1=[O:68])(=[O:13])[CH3:12]Participants
10
Reactant 5
Product 2
Reagents, catalysts & solvents 3
Procedure
HOBT (27 mg, 0.2 mmol), acetic acid (12.5 μL, 0.22 mmol), DIPEA (35 μl, 0.2 mmol) and then EDCI (48 mg, 0.25 mmol) were added to a solution of N-[1-(2-aminoethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide trifluoroacetate (Method 9, 100 mg, 0.2 mmol) in DCM (2 mL) and THF (0.5 mL). The reaction was stirred for 90 mins at ambient temperature, diluted with EtOAc (5 mL), washed with 1 N NaOH (3 mL), 1 N HCl (3 mL), saturated aqueous NaHCO3 solution (5 mL) and dried (MgSO4). Column chromatography (7:3 to 8:2 EtOAc:isohexane) gave the title compound (40 mg, 47%) as a tan solid.
Workup
- washwashed with 1 N NaOH (3 mL), 1 N HCl (3 mL), saturated aqueous NaHCO3 solution (5 mL)
- dry with materialdried (MgSO4)
Sources & evidence
- ORD record
- ord-21e47faca51640da97addb42aca9012c
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169927B2
Reaction notes
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