Dimethylformamide → HCID 68488914, compound

HRID 1991208Notes

Reaction equation

HRID 1991208 reaction equation
Br[C:2]1[C:7]2[N:8]([CH2:11][C:12]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)=[O:13])[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:25][N:26](C=O)C>>[C:25]([C:2]1[C:7]2[N:8]([CH2:11][C:12]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[CH:16]=3)=[O:13])[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:26]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 11440680HCID 11440680, compound

Product 1

HCID 68488914HCID 68488914, compound

Procedure

To a solution of 2-(7-bromo-1H-benzoimidazol-1-yl)-N-(3,5-dimethoxyphenyl)acetamide (Example 52) (50 mg, 0.13 mmol) in dry DMF (0.64 mL) copper(I) cyanide (23 mg, 0.26 mmol) was added. The mixture was irradiated in a microwave oven at 200° C. for 60 min. The reaction mixture was partitioned between ethyl acetate and water. The organic extract was concentrated and the residue was purified by preparative HPLC to yield the title compound, 20 mg (46%). MS (ESI) m/z: 337.2 [M+H). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.69 (s, 6 H) 5.39 (s, 2H) 6.23 (t, J=2.3 Hz, 1H) 6.80 (d, J=2.0 Hz, 2 H) 7.37 (t, J=7.8 Hz, 1H) 7.74 (d, J=7.1 Hz, 1H) 8.05 (dd, J=8.1, 1.0 Hz, 1H) 8.40 (s, 1H) 10.47 (s, 1H).

Workup

  1. customThe mixture was irradiated in a microwave oven at 200° C. for 60 min
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. concentrationwas concentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-080be19561bf490f9aa5f718aa8e270b
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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