Potassium Carbonate → HCID 57757976, compound

HRID 229624Notes

Reaction equation

HRID 229624 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[C:9]([CH:11]=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.S([CH2:32][N+:33]#[C-:34])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([C:8]2[C:9]([C:11]3[O:12][CH:34]=[N:33][CH:32]=3)=[CH:10][N:6]3[C:7]=2[C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 57757971HCID 57757971, compound2×

Product 1

HCID 57757976HCID 57757976, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde (Intermediate H, Step 2) (692 mg, 2.44 mmol) was added tosylmethyl isocyanide (477 mg, 2.44 mmol) and potassium carbonate (338 mg, 2.44 mmol) in MeOH. The solution was allowed to stir at reflux overnight. The solution was dried and diluted with EtOAc (50 mL) and THF (50 mL). Water (50 mL) was added to the reaction mixture. The solution was transferred to a separatory funnel, and the organic layer was isolated and washed with brine (50 mL). The aqueous layers were back extracted with EtOAc (2×50 mL). The combined organic layers were collected, dried (Na2SO4), concentrated onto silica gel, and purified by column chromatography (100% CH2Cl2 ramping to 95:5 v/v CH2Cl2-EtOAc) to afford 310 mg of the above compound as an yellow solid (yield 39%). 1H-NMR (DMSO-d6) δ 11.70 (s, 1H), 8.31 (d, J=8.5 Hz, 2H), 8.28 (s, 1H), 8.17 (s, 1H), 7.66 (d, J=7.1 Hz, 2H), 6.75 (s, 1H); MS [M+H]+=323.2; LCMS RT=2.57 min.

Workup

  1. temperatureat reflux overnight
  2. customThe solution was dried
  3. additiondiluted with EtOAc (50 mL) and THF (50 mL)
  4. additionWater (50 mL) was added to the reaction mixture
  5. customThe solution was transferred to a separatory funnel
  6. customthe organic layer was isolated
  7. washwashed with brine (50 mL)
  8. extractionThe aqueous layers were back extracted with EtOAc (2×50 mL)
  9. customThe combined organic layers were collected
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated onto silica gel
  12. custompurified by column chromatography (100% CH2Cl2 ramping to 95:5 v/v CH2Cl2-EtOAc)

Sources & evidence

ORD record
ord-0484f11468bb41caa5f43adb6d5eca75
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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