Dimethylformamide → HCID 74928828, compound

HRID 504493Notes

Reaction equation

HRID 504493 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[F:38])[C:5]2=[CH:4][CH:3]=1.Cl.CNC.CCN=C=N[CH2:49][CH2:50][CH2:51]N(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:75][N:76]([CH:78]=[O:79])[CH3:77]>>[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:50]([C:78](=[O:79])[N:76]([CH3:77])[CH3:75])([CH3:51])[CH3:49])[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[F:38])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 6

HCID 6228DimethylformamideHCID 10473Dimethylamine, hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 77502807HCID 77502807, compound

Product 1

HCID 74928828HCID 74928828, compound

Procedure

A mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(2-hydroxycarbonyl-2-methyl-ethoxy)-phenyl]-2′-(2,5-difluoro phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (100 mg, 0.174 mmol), dimethylamine hydrochloride (28 mg, 0.348 mmol), EDC.HCl (66 mg, 0.348 mmol), HOBt (47 mg, 0.348 mmol) and DIPEA (135 mg, 1.044 mmol) in anhydrous DMF (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 the 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-6fbc3d0ed43a408e8fa73ce13e92b74c
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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