Tert-Butylamine → HCID 66661120, compound

HRID 408873Notes

Reaction equation

HRID 408873 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.C(N(CC)CC)C.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[C:18]([NH:22][C:8](=[O:10])[C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 27628204-Methylpyridine-2-carboxylic acid

Product 1

HCID 66661120HCID 66661120, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylpyridine-2-carboxylic acid (500 mg, 3.65 mmol), triethylamine (1.27 g, 12.5 mmol, 1.75 mL) and tert-butylamine (267 mg, 3.65 mmol) were combined and stirred in dichloromethane (1 mL). 1-Propanephosphonic acid cyclic anhydride (4.82 g, 7.5 mmol, 4.5 mL, 50% solution in ethyl acetate) was added dropwise and the reaction stirred at room temperature for 1 hour. The reaction mixture was concentrated at reduced pressure and the resulting residue taken up in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over sodium sulfate and concentrated under vacuum to afford the title compound (376 mg). MS (ESI) m/z 193.4 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated at reduced pressure
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-56b48c9a327b4901b2f453bf902d264d
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

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