Dimethylformamide → HCID 11791855, compound

HRID 1490319Notes

Reaction equation

HRID 1490319 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:4].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.CN(C=O)C.[OH-].[K+]>O>[C:22]1([C:19]2[CH:18]=[CH:17][C:16]([NH:15][CH2:2][C:3]([NH:5][C:6]3[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=3[C:8]([OH:10])=[O:9])=[O:4])=[CH:21][CH:20]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 71024-AminobiphenylHCID 14797Potassium HydroxideHCID 10611190HCID 10611190, compound

Product 1

HCID 11791855HCID 11791855, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(N-bromoacetylamino)benzoic acid from Example 79 (8.00 g, 31.0 mmol), para-aminobiphenyl (13.12 g, 77.5 mmol) and DMF (80 mL) was heated to 80° C. for 8 h. The mixture was cooled, poured over H2O (1 L) and 5% KOH (300 mL) and washed with CH2Cl2 (3×300 mL). The aqueous layer was acidified to pH 2 with 2N HCl, cooled below room temperature and filtered. The filter cake was rinsed with cold water (100 mL) and dried under high vacuum at 45° C. The resulting air-sensitive material was triturated with ethyl acetate (100 mL), filtered, and rinsed with ethyl acetate (2×25 mL) to yield, after drying, 8.18 g (76%) of the title compound as a tan solid; 1H NMR (DMSO-d6) δ 13.4 (broad s, 1H), 12.05 (s, 1H), 8.75 (d, J=8.4, 1H), 7.95 (dd, J=7.4, J=1.2, 1H), 7.60 (td, J=7.2, J=1.2, 1H), 7.54 (d, J=7.6, 2H), 7.45 (d, J=8.8, 2H), 7.37 (t, J=7.6, 2H), 7.22 (t, J=7.6, 1H), 7.13 (t, J=7.6, 1H), 6.69 (d, J=8.4, 2H), 6.7 (broad s, 1H), 3.90 (s, 2H); 13C NMR (DMSO-d6) a 170.74, 169.12, 147.71, 140.60, 140.36, 134.20, 131.14, 128.87, 128.74, 127.28, 125.96, 125.55, 122.69, 119.40, 115.97, 112.85, 48.87; MS (EI, m/z) 328 (M-H2O+).

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with CH2Cl2 (3×300 mL)
  3. temperaturecooled below room temperature
  4. filtrationfiltered
  5. washThe filter cake was rinsed with cold water (100 mL)
  6. customdried under high vacuum at 45° C
  7. customThe resulting air-sensitive material was triturated with ethyl acetate (100 mL)
  8. filtrationfiltered
  9. washrinsed with ethyl acetate (2×25 mL)
  10. customto yield
  11. customafter drying

Sources & evidence

ORD record
ord-f8774cc15f0d42a0931eaa4083b2ec13
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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