Methylamine → HCID 15952000, compound

HRID 1927367Notes

Reaction equation

HRID 1927367 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:17](=[S:18])[N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)[C:15](=[O:31])[C:11]32[CH2:14][CH2:13][CH2:12]3)=[CH:6][CH:5]=1.[CH3:33][NH2:34]>>[CH3:33][NH:34][C:3](=[O:2])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:17](=[S:18])[N:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:29])([F:30])[F:28])[CH:20]=3)[C:15](=[O:31])[C:11]32[CH2:12][CH2:13][CH2:14]3)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86609864HCID 86609864, compound

Product 1

HCID 15952000HCID 15952000, compoundYield 84%

Procedure

A mixture of 4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]-benzoic acid methyl ester (51b) (0.046 g, 0.1 mmol) and methylamine (1 ml distilled from its 40% aqueous solution) was kept at −20° C. for 15 hours. After evaporation of the methylamine, the mixture was chromatographed (dichloromethane:acetone, 80:20) to yield N -methyl-4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]oct-5-yl]benzamide (51c) [RD161] (0.041 g, 0.085, 84%), the structure of which is illustrated in Formula 27.

Workup

  1. customAfter evaporation of the methylamine
  2. customthe mixture was chromatographed (dichloromethane:acetone, 80:20)

Sources & evidence

ORD record
ord-af789efe4732409d99e6f64d9b968617
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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