Diisopropylethylamine → HCID 18682370, compound

HRID 277185Notes

Reaction equation

HRID 277185 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:58][O:59][C:60](=[O:75])[CH2:61][CH:62]([N:64]1[CH2:69][CH2:68][NH:67][CH:66]([CH2:70][CH:71]([CH3:73])[CH3:72])[C:65]1=[O:74])[CH3:63]>CN(C=O)C.O>[CH3:58][O:59][C:60](=[O:75])[CH2:61][CH:62]([N:64]1[CH2:69][CH2:68][N:67]([C:17](=[O:19])[CH2:16][C:13]2[CH:12]=[CH:11][C:10]([NH:9][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[CH3:21])=[O:20])=[CH:15][CH:14]=2)[CH:66]([CH2:70][CH:71]([CH3:72])[CH3:73])[C:65]1=[O:74])[CH3:63]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acidHCID 18682369HCID 18682369, compound

Product 1

HCID 18682370HCID 18682370, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of [4-(3-o-tolyl-ureido)-phenyl]-acetic acid (55 mg, 0.19 mmol), diisopropyl ethyl amine (0.17 ml), BOP (86 mg, 0.19 mmol) in DMF (1 ml) was added 3-(3-isobutyl-2-oxo-piperazin-1-yl)-butyric acid methyl ester (50 mg, 0.19 mmol). After stirring 16 h at room temperature the solution was diluted with water and extracted into ethyl acetate. The combined organics were washed with 5% citric acid, saturated NaHCO3, and brine; dried over MgSO4, filtered, and concentrated under reduced pressure. Column chromatography on silica gel eluting with 2% MeOH/CH2Cl2 gave 20 mg of the title compound as a yellow amorphous solid. MS [M+1]+523.3.

Workup

  1. extractionextracted into ethyl acetate
  2. washThe combined organics were washed with 5% citric acid, saturated NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8c7531f4dc04370aeae7f86cad21ef7
Source dataset
uspto-grants-2002_03
Patent number
US06355662B1

Reaction notes

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