Methylamine → HCID 86609859, compound

HRID 1927356Notes

Reaction equation

HRID 1927356 reaction equation
S(Cl)(Cl)=O.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:20](=[O:21])[C:16]3([CH2:19][CH2:18][CH2:17]3)[N:15]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=O)=[CH:24][CH:23]=3)[C:14]2=[S:32])=[CH:9][C:8]=1[C:33]([F:36])([F:35])[F:34])#[N:6].[CH3:37][NH2:38]>C1COCC1>[CH3:37][NH:38][C:29](=[O:31])[CH2:28][C:25]1[CH:24]=[CH:23][C:22]([N:15]2[C:14](=[S:32])[N:13]([C:10]3[CH:11]=[CH:12][C:7]([C:5]#[N:6])=[C:8]([C:33]([F:35])([F:36])[F:34])[CH:9]=3)[C:20](=[O:21])[C:16]32[CH2:19][CH2:18][CH2:17]3)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24386Thionyl ChlorideHCID 86609858HCID 86609858, compound

Product 1

HCID 86609859HCID 86609859, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (0.238 g, 2 mmol) was added dropwise to a mixture of {4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}acetic acid (46c) (0.357 g, 0.777 mmol) in THF (5 ml) cooled to 0° C. The mixture was stirred for 1 hour at room temperature and then methylamine (0.5 ml) was added into the mixture. The mixture was stirred for an additional 2 hours. The medium was filtered and the filtrate was concentrated and chromatographed (dichloromethane:acetone, 80:20) to yield N-methyl-2-{4-[7-(4-cyano-3-trifluoromethylphenyl)-8-oxo-6-thioxo-5,7-diaza-spiro[3.4]oct-5-yl]phenyl}acetamide (46e) [RD149] (0.348 g, 0.738 mmol, 95%), the structure of which is illustrated in Formula 18, as an off-white powder.

Workup

  1. stirringThe mixture was stirred for an additional 2 hours
  2. filtrationThe medium was filtered
  3. concentrationthe filtrate was concentrated
  4. customchromatographed (dichloromethane:acetone, 80:20)

Sources & evidence

ORD record
ord-5a5bd5355a0f4bf291d32df4ebbea3c7
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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