Tetrahydrofuran → HCID 74830393, compound

HRID 504488Notes

Reaction equation

HRID 504488 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.Cl.[F:41][C:42]1([F:48])[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1.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>>[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][C:65]([CH3:64])([CH3:66])[C:82]([N:45]4[CH2:46][CH2:47][C:42]([F:48])([F:41])[CH2:43][CH2:44]4)=[O:83])[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

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 77502936HCID 77502936, compound

Product 1

HCID 74830393HCID 74830393, compound

Procedure

In a manner similar to the method described in Example 27, 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) was reacted with 4,4-difluoropiperidine hydrochloride (83 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) to give title compound as a white solid (40 mg).

Sources & evidence

ORD record
ord-0fd9ac05404745f29c7ec9a3f06f63f0
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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