Tetrahydrofuran → HCID 74928746, compound

HRID 504487Notes

Reaction equation

HRID 504487 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]([F:46])([F:45])[CH2:43][NH2:44].CCN=C=N[CH2:52][CH2:53][CH2:54]N(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C1C[O:81][CH2:80]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:53]([CH3:54])([C:80](=[O:81])[NH:44][CH2:43][C:42]([F:46])([F:45])[F:41])[CH3:52])[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 97722,2,2-Trifluoroethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 77502936HCID 77502936, compound

Product 1

HCID 74928746HCID 74928746, 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 2,2,2-trifluoroethylamine hydrochloride (71 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 (50 mg).

Sources & evidence

ORD record
ord-fa5af606612343debbe8f4bf6e7bc25b
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

Loading…