Acetic Acid → HCID 178419329, compound

HRID 1433234Notes

Reaction equation

HRID 1433234 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2N=N1.C(N([CH2:42][CH3:43])CC)C.[C:44]([OH:47])(=O)[CH3:45].[C:48](#N)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:45]([CH2:44][O:47][C:20]3[CH:25]=[CH:24][C:23]([CH:43]4[CH2:42][CH2:48]4)=[CH:22][CH:21]=3)=[N:9][C:4]=2[CH:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6342Acetonitrile2×HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 178419329HCID 178419329, compoundYield 77%

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-benzene-1,2-diamine (0.759 g, 4.06 mmol), BOP (1.381 g, 3.12 mmol), and triethylamine (0.44 mL, 3.12 mmol) in acetonitrile (18 mL) were added dropwise over 2 hours a solution of 4-cyclopropyl-phenoxy)-acetic acid (0.600 g, 3.12 mmol) in acetonitrile (5 mL). The reaction mixture was stirred for 12 hours followed by heating at 80° C. for another 8 hours. The reaction mixture was concentrated under reduced pressure to provide a residue, which was purified by chromatography (silica, hexanes: EtOAc=1:1) to afford the title compound as a yellow solid (0.825 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto provide a residue, which
  3. customwas purified by chromatography (silica, hexanes: EtOAc=1:1)

Sources & evidence

ORD record
ord-64daefd72e9c45eca45386eebc9c7f74
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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