Dimethylamine → HCID 86609863, compound

HRID 245016Notes

Reaction equation

HRID 245016 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:16](=[O:17])[C:12]3([CH2:15][CH2:14][CH2:13]3)[N:11]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24]OS(C)(=O)=O)=[CH:20][CH:19]=3)[C:10]2=[S:30])=[CH:5][C:4]=1[C:31]([F:34])([F:33])[F:32])#[N:2].[CH3:35][NH:36][CH3:37]>C1COCC1>[CH3:35][N:36]([CH2:24][C:21]1[CH:20]=[CH:19][C:18]([N:11]2[C:10](=[S:30])[N:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([C:31]([F:32])([F:34])[F:33])[CH:5]=3)[C:16](=[O:17])[C:12]32[CH2:15][CH2:14][CH2:13]3)=[CH:23][CH:22]=1)[CH3:37]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86609862HCID 86609862, compound

Product 1

HCID 86609863HCID 86609863, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of Methanesulfonic acid 4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]phenylmethyl ester (50a) (0.02 g, 0.039 mmol) and dimethylamine (0.5 ml; distilled from its 40% aqueous solution) in THF (1 ml) was stirred for 2 hours at −78° C. The mixture was concentrated and chromatographed (dichloromethane:acetone, 95:5; acetone) to yield 4-[5-(4-dimethylaminomethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-7-yl]-2-trifluoromethylbenzonitrile (50c) [RD156] (0.017 g, 0.037 mmol, 95%), the structure of which is illustrated in Formula 24, as a white powder.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (dichloromethane:acetone, 95:5; acetone)

Sources & evidence

ORD record
ord-88f8bd5e84ed45138104ded8f6bb38a5
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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