Methyl isothiocyanate → HCID 86672871, compound

HRID 2403699Notes

Reaction equation

HRID 2403699 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[NH2:28])[C:5]([N:7]1[CH2:12][CH2:11][C:10]2([CH2:20][C:19](=[O:21])[C:18]3[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=[CH:15][C:14]=3[CH2:13]2)[CH2:9][CH2:8]1)=[O:6].[N:29]([CH3:32])=[C:30]=[S:31]>O1CCCC1>[NH2:1][C:2]1[CH:3]=[C:4]([C:5]([N:7]2[CH2:12][CH2:11][C:10]3([CH2:20][C:19](=[O:21])[C:18]4[N:17]([CH:22]([CH3:24])[CH3:23])[N:16]=[CH:15][C:14]=4[CH2:13]3)[CH2:9][CH2:8]2)=[O:6])[CH:25]=[CH:26][C:27]=1[NH:28][C:30]([NH:29][CH3:32])=[S:31]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 86672872HCID 86672872, compound

Product 1

HCID 86672871HCID 86672871, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1′-(3,4-diaminobenzoyl)-1-isopropyl-4,6-dihydrospiro[indazole-5,4′-piperidin]-7(1H)-one (0.1 g, 0.3 mmol) and isothiocyanatomethane (19 mg, 0.3 mmol) was dissolved in tetrahydrofuran (3 mL). The reaction was heated to reflux and stirred for 6 hours. The reaction mixture was concentrated, and the residue was poured into cold water. The solution was extracted with ethyl acetate (3×20 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated to provide 1-(2-amino-4-(1-isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-ylcarbonyl)phenyl)-3-methylthiourea (37 mg, 27%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was poured into cold water
  5. extractionThe solution was extracted with ethyl acetate (3×20 mL)
  6. dry with materialThe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6e6aa072b53b47d29b3d3285ecdde141
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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