Methylamine → HCID 86609861, compound

HRID 245015Notes

Reaction equation

HRID 245015 reaction equation
[CH3:1][NH2:2].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:18](=[O:19])[C:14]3([CH2:17][CH2:16][CH2:15]3)[N:13]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26]OS(C)(=O)=O)=[CH:22][CH:21]=3)[C:12]2=[S:32])=[CH:7][C:6]=1[C:33]([F:36])([F:35])[F:34])#[N:4]>C1COCC1>[CH3:1][NH:2][CH2:26][C:23]1[CH:22]=[CH:21][C:20]([N:13]2[C:12](=[S:32])[N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]#[N:4])=[C:6]([C:33]([F:36])([F:34])[F:35])[CH:7]=3)[C:18](=[O:19])[C:14]32[CH2:17][CH2:16][CH2:15]3)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86609862HCID 86609862, compound

Product 1

HCID 86609861HCID 86609861, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Methylamine (0.5 ml) was bubbled into 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) (0.059 g, 0.115 mmol) in THF (3 ml) cooled to −78° C. After 1 hour of reaction at −78° C., the mixture was concentrated and chromatographed (dichloromethane:acetone, 95:5; methanol) to yield 4-[5-(4-methylaminomethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-7-yl]-2-trifluoromethylbenzonitrile (50b) [RD155] (0.042 g, 0.095 mmol, 82%), the structure of which is illustrated in Formula 23, as a white powder.

Workup

  1. customAfter 1 hour of reaction at −78° C.
  2. concentrationthe mixture was concentrated
  3. customchromatographed (dichloromethane:acetone, 95:5; methanol)

Sources & evidence

ORD record
ord-3a8fe73a73d946329a827ea234e707d4
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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