Potassium Carbonate → HCID 68699541, compound

HRID 639709Notes

Reaction equation

HRID 639709 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[N:5]([C:14]1[CH:19]=[C:18]([CH:20]=[O:21])[N:17]=[C:16]([NH2:22])[C:15]=1[N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2].C1(C)C=CC(S([CH2:36][N+:37]#[C-:38])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:3][C:4](=[O:26])[N:5]([C:14]1[CH:19]=[C:18]([C:20]2[O:21][CH:38]=[N:37][CH:36]=2)[N:17]=[C:16]([NH2:22])[C:15]=1[N+:23]([O-:25])=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([CH3:13])=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86614493HCID 86614493, compound

Product 1

HCID 68699541HCID 68699541, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2-Amino-6-formyl-3-nitro-pyridin-4-yl)-(6-methyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester (190 mgs/0.529 mmols) was dissolved in MeOH (5 mls). Added (4-tolylsulphonyl)methylisocyanide (124 mgs/0.634 mmols) followed by anhydrous potassium carbonate (200 mgs/1.45 mmols). Stirred under N2 for 1 hr then concentrated in vacuo. Partitioned between EtOAc (100 mls) and H2O (50 mls). Organic collected, washed with brine, dried over Na2SO4, filtered and concentrated to a black resin. Purification by column chromatography eluting with 90:10 DCM/MeOH gave the title compound (135 mgs) as a crude brown solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPartitioned between EtOAc (100 mls) and H2O (50 mls)
  3. washOrganic collected, washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a black resin
  7. customPurification by column chromatography
  8. washeluting with 90:10 DCM/MeOH

Sources & evidence

ORD record
ord-d943396155134e86b6cbf2d8a189d51b
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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