Methylamine → HCID 58835250, compound

HRID 1660917Notes

Reaction equation

HRID 1660917 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:14]([C:15]([OH:17])=O)=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1NC=CN=1)([C:20]1[NH:21]C=CN=1)=O.CN.C(Cl)Cl>CN(C=O)C.C1COCC1.CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:10]=[CH:11][N:12]=[CH:13][C:14]=1[C:15]([NH:21][CH3:20])=[O:17])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6329MethylamineHCID 6344DichloromethaneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 221726234-{[(Tert-butoxy)carbonyl]amino}pyridine-3-carboxylic acid

Product 1

HCID 58835250HCID 58835250, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The acid, 4-tert-Butoxycarbonylamino-nicotinic acid (1.0 g, 4.20 mmol) was suspended in dry DMF (50 mL) followed by carbonyl-diimidazole (CDI, 1.36 g, 8.40 mmol). The mixture was heated to 60° C. for 1 h, then cooled. Methyl amine in THF was added to the solution followed by evaporation of the mixture. The residue was dissolved in water (20 mL)/chloroform (50 mL) and shaken then the layers separated. The aqueous layer was extracted further with chloroform (3×50 mL) and the combined organic extracts dried (MgSO4) and evaporated to give a yellow oily solid. Silica gel chromatography (CH2Cl2, 0-15% MeOH gradient) gave the desired product, (3-(N-methylaminocarbonyl)-pyridin-4-yl)-carbamic acid tert-butyl ester, as a yellow solid.

Workup

  1. temperaturecooled
  2. customfollowed by evaporation of the mixture
  3. dissolutionThe residue was dissolved in water (20 mL)/chloroform (50 mL)
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted further with chloroform (3×50 mL)
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. customevaporated
  8. customto give a yellow oily solid

Sources & evidence

ORD record
ord-ba0bb7047401424ca8e5cf56ab087375
Source dataset
uspto-grants-2011_10
Patent number
US08030318B2

Reaction notes

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