Methylamine → HCID 59004534, compound

HRID 1255140Notes

Reaction equation

HRID 1255140 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([CH:12]=O)[N:11]=1)=[O:5].[CH3:29][NH2:30].S([CH2:41][N+:42]#[C-:43])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CCO.CC(O)=O>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:10]([C:12]2[N:30]([CH3:29])[CH:41]=[N:42][CH:43]=2)[N:11]=1)=[O:5]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 24765490HCID 24765490, compound

Product 1

HCID 59004534HCID 59004534, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Into a solution of Compound 67 (206 mg, 0.5 mmol) and MeNH2 (2.0 M in MeOH, 1.25 mL) in 10 mL of EtOH was added HOAc (0.15 mL). The solution was heated under reflux for 2 hours, cooled to room temperature. The solution was treated with tosylmethyl isocyanide (0.75 mmol) and K2CO3 (2 mmol). The mixture was stirred under reflux for 2 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and 1 N NaOH aq. solution. The organic phase was washed with water, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel (eluted with MeOH in CH2Cl2) to give Compound 80 (125 mg, 54%) as a yellow solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureunder reflux for 2 hours
  4. concentrationThe reaction mixture was concentrated
  5. custompartitioned between ethyl acetate and 1 N NaOH aq. solution
  6. washThe organic phase was washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (eluted with MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-d28357f0554d4f0c8ccddb0f455e09c8
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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