Dimethylamine, hydrochloride → HCID 74928748, compound

HRID 504499Notes

Reaction equation

HRID 504499 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][C:24]([C:27]([OH:29])=O)([CH3:26])[CH3:25])[CH2:14][C:13](=[O:30])[NH:12][CH:11]3[C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=3[F:38])[C:5]2=[CH:4][CH:3]=1.Cl.[CH3:41][NH:42][CH3:43].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>CN(C)C1C=CN=CC=1.C1COCC1>[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:24]([C:27](=[O:29])[N:42]([CH3:43])[CH3:41])([CH3:26])[CH3:25])[CH2:14][C:13](=[O:30])[NH:12][CH:11]3[C:31]3[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=3[F:38])[C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 76568130HCID 76568130, compound

Product 1

HCID 74928748HCID 74928748, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of racemic (2′R,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(5-chloro-2-fluoro-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (30 mg), dimethylamine hydrochloride (8.5 mg), 4-dimethylamino pyridine (18 mg), EDCl (21 mg) and DIPEA (129 mg) in THF (4 mL) was stirred at room temperature overnight. Then the solvent was removed and the residue was separated by preparative HPLC to give title compound as white solid (7 mg).

Workup

  1. customThen the solvent was removed
  2. customthe residue was separated by preparative HPLC

Sources & evidence

ORD record
ord-e4d7226c318e4289852b96b1f67d8bc1
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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