Tetrahydrofuran → HCID 74928808, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:39])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23]CC(C(O)=O)C)[CH2:14][C:13](=[O:30])[NH:12][CH:11]3[C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH3:38])[C:5]2=[CH:4][CH:3]=1.[C:40]([N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)(=[O:42])[CH3:41].CCN=C=NCCCN(C)C.Cl.C1C=C[C:64]2N(O)N=N[C:65]=2[CH:66]=1.CCN(C(C)C)C(C)C.C1C[O:83][CH2:82]C1>>[C:40]([N:43]1[CH2:48][CH2:47][N:46]([C:82](=[O:83])[C:65]([CH3:64])([CH3:66])[O:23][C:17]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=2[CH:15]2[CH2:14][C:13](=[O:30])[NH:12][CH:11]([C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH3:38])[C:10]32[C:5]2[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:8][C:9]3=[O:39])[CH2:45][CH2:44]1)(=[O:42])[CH3:41]Participants
7
Procedure
A mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-hydroxycarbonyl-2-methyl-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (150 mg, 0.263 mmol), N-acetylpiperazine (67 mg, 0.526 mmol), EDC.HCl (100 mg, 0.526 mmol), HOBt (71 mg, 0.526 mmol) and DIPEA (204 mg, 1.579 mmol) in anhydrous THF (3 mL) was stirred at room temperature overnight. Then the mixture was filtered and the filtrate was concentrated. The residue was purified by Prep-HPLC to give title compound as a white solid (40 mg).
Workup
- filtrationThen the mixture was filtered
- concentrationthe filtrate was concentrated
- customThe residue was purified by Prep-HPLC
Sources & evidence
- ORD record
- ord-c15017c42bb2428db50c7bb7a60d4be8
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776875B2
Reaction notes
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