Formic Acid → HCID 86610957, compound

HRID 2250396Notes

Reaction equation

HRID 2250396 reaction equation
[CH3:1][C:2]1[C:3]([NH:13]C(OC(C)(C)C)=O)=[N:4][C:5](C(O)=O)=[CH:6][C:7]=1[O:8][CH3:9].[CH:21]([OH:23])=[O:22]>>[CH3:1][C:2]1[C:3]([NH2:13])([C:21]([OH:23])=[O:22])[NH:4][CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 68461294HCID 68461294, compound2×

Product 1

HCID 86610957HCID 86610957, compound

Conditions

Temperature
40 °C

Procedure

2.87 g of methyl 2-tert-butyloxycarbonylamino-4-methoxy-pyridin-6-carboxylic acid (compound D3) are dissolved in 72 ml of formic acid. Subsequently, the solution is warmed to 40° C. for 2.5 h. After completion of the reaction, the solution is concentrated in vacuum and coevaporated with toluene. The remaining residue is redissolved in 150 ml of dichloromethane and extracted three times each with 50 ml of sat sodium hydrogencarbonate solution. The organic layer is dried using sodium sulphate, filtered with suction and concentrated in vacuum to yield 1.85 g of the title compound as a colorless oil. ESI-MS: 183.1 [MH+]. TLC: Rf=0.28 (dichloromethane/methanol 10:1).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe solution is concentrated in vacuum
  3. dissolutionThe remaining residue is redissolved in 150 ml of dichloromethane
  4. extractionextracted three times each with 50 ml of sat sodium hydrogencarbonate solution
  5. customThe organic layer is dried
  6. filtrationfiltered with suction
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0c584d86126d4bd389d9ed2210873d2d
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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