4-Bromobenzoic acid → HCID 68407394, compound

HRID 888022Notes

Reaction equation

HRID 888022 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25])=[O:17])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:6](=[O:8])[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 114644-Bromobenzoic acidHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

Product 1

HCID 68407394HCID 68407394, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4,6-Dimethoxy-1,3,5-triazinyl-2-yl)-4-methylmorpholinium chloride (Method 18; 5.4 g, 19.4 mmol) was added to a solution of 4-bromobenzoic acid (3.5 g, 17.4 mmol) and 1-(N-t-butoxycarbonylamino)-2-aminobenzene (Method 17; 4.3 g, 20.9 mmol) in DMF (100 ml) and stirred at ambient temperature for 20 hours. The reaction mixture was partitioned between water and ethyl acetate. The organics were washed with a saturated aqueous solution of sodium hydrogen carbonate, water, 1M aqueous hydrochloric acid, water and brine, before being dried over magnesium sulfate. The organics were then evaporated to give the title compound (7.1 g, quantitative), which was used without further purification. NMR Spectrum: (DMSO-d6): 1.45 (s, 9H), 7.18 (m, 2H), 7.54 (m, 2H), 7.76 (d, 2H), 7.90 (d, 2H), 8.63 (s, 1H), 9.86 (s, 1H); Mass Spectrum: (M+H+-Boc) 291.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organics were washed with a saturated aqueous solution of sodium hydrogen carbonate, water, 1M aqueous hydrochloric acid, water and brine
  3. dry with materialbefore being dried over magnesium sulfate
  4. customThe organics were then evaporated

Sources & evidence

ORD record
ord-119de5b162cd480c95f97b63fca1948c
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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