Dimethylamine, hydrochloride → HCID 86631797, compound

HRID 1095163Notes

Reaction equation

HRID 1095163 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]([C:36](O)=[O:37])([CH3:35])[CH3:34])=[C:6]([CH:8]2[C:13]3(C4C(=CC(Cl)=CC=4)N[C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1.C[CH2:40][N:41]=[C:42]=NCCCN(C)C.[CH:50]1[CH:51]=[CH:52][C:53]2N(O)N=[N:56][C:54]=2[CH:55]=1.CCN(C(C)C)C(C)C.[ClH:69].CNC>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][C:33]([C:36](=[O:37])[N:41]([CH3:42])[CH3:40])([CH3:35])[CH3:34])=[C:6]([CH:8]2[C:13]3([C:53]4[C:54](=[CH:55][C:50]([Cl:69])=[CH:51][CH:52]=4)[NH:56][C:14]3=[O:23])[CH:12]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[CH2:11][C:10](=[O:31])[NH:9]2)[CH:7]=1

Participants

7

Reactant 5

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 76568082HCID 76568082, compound

Product 1

HCID 86631797HCID 86631797, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of racemic(2′R, 3R, 4′S)-2′-[5-bromo-2-(1-hydroxycarbonyl-1-methyl-ethoxy)-phenyl]-6-chloro-4′-(3-chlorophenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.065 mmol), EDCI (18.7 mg, 0.098 mmol), HOBt (15 mg, 0.098 mmol) and DIPEA (75 mg, 0.6 mmol) in THF (2 mL) was added dimethylamine hydrochloride (20 mg, 0.25 mmol). The mixture was stirred at room temperature overnight, purified by prep-HPLC to give the title compound as a white solid (26 mg).

Workup

  1. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-6c88240bb58f473681251823073f7810
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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