Tetrahydrofuran → HCID 74928807, compound

HRID 504485Notes

Reaction equation

HRID 504485 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.[CH3:41][NH:42][CH3:43].[CH3:44]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:75]1C[O:78][CH2:77][CH2:76]1>>[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:76]([C:77](=[O:78])[N:42]([CH3:43])[CH3:41])([CH3:75])[CH3:44])[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 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 77502936HCID 77502936, compound

Product 1

HCID 74928807HCID 74928807, compound

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 in Example 1f (150 mg, 0.263 mmol), dimethylamine hydrochloride (43 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 (50 mg).

Workup

  1. filtrationThen the mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-f307798a1e7545ecb0ce39228cd4f170
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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