Butylamine → HCID 22046473, compound

HRID 1830717Notes

Reaction equation

HRID 1830717 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:14].[CH2:22]([NH2:26])[CH2:23][CH2:24][CH3:25].C(N(C(C)C)CC)(C)C>CN1C(=O)CCC1.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:22]([NH:26][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])[CH:5]=1)[CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 3

HCID 8007ButylamineHCID 81531DiisopropylethylamineHCID 22046509HCID 22046509, compound

Product 1

HCID 22046473HCID 22046473, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirred solution of 4-Methoxy-3-(3-pyrazin-2-yl-ureido)-benzoic acid (32 mg; 0.11 mmol) in N-methyl pyrrolidinone (1 mL) was added O-benzotrazol-1-yl-N,N,N′,N′-tetramethyl-uronium hexafluorophosphate (HBTU; 45 mg; 0.12 mmol), butyl amine (12 μL; 0.12 mmol), and diisopropylethylamine (35 μL; 0.20 mmol). The reaction was stirred at room temperature for 12 hours. The reaction was diluted with ethyl acetate (20 mL) and 10% aqueous sodium carbonate (20 mL) and stirred for 5 minutes. A precipitate formed which was filtered and dried under reduced pressure to yield an off white solid (49% yield).

Workup

  1. stirringstirred for 5 minutes
  2. customA precipitate formed which
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ae0e61902e6459081167540bd906931
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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