Acrylamide → HCID 69585165, compound

HRID 1243152Notes

Reaction equation

HRID 1243152 reaction equation
[CH2:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=2)=[O:20])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)[CH:2]([CH3:4])[CH3:3].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:56]([NH2:60])(=[O:59])[CH:57]=[CH2:58].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH2:1]([O:5][C:6](=[O:33])[NH:7][C:8]1([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])=[CH:24][CH:23]=2)=[O:20])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](/[CH:58]=[CH:57]/[C:56]([NH2:60])=[O:59])[CH:14]=2)[CH2:9]1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 6579AcrylamideHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 69585193HCID 69585193, compound

Product 1

HCID 69585165HCID 69585165, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a 10 ml pressure tube, the bromide from Example 42B (125 mg, 0.24 mmol), palladium(II)acetate (2.7 mg, 0.012 mmol), tri-o-tolylphosphine (110 mg, 0.36 mmol), acrylamide (34 mg, 048 mmol), triethylamine (0.12 ml, 0.8 mmol) and DMF (2 ml) were added. After purging with nitrogen, the reaction mixture was heated at 110° C. for overnight. The reaction mixture was partitioned between methylene chloride and water. The organic layer was washed with brine and concentrated under reduced pressure. The residue was purified on column of silica gel to provide the titled compound (115 mg, 95%) as a white solid. 1HNNMR (DMSO-d6, 300 MHz), δ 9.13 (b, 1H, NH), 7.45 and 7.30 (b, 2H, NH2), 7.01 (b, 1H, NH), 7.36, 7.32, 6.56 and 6.52 (AB, J=12 Hz, 2H, CH═CH), 7.32, 7.30, 6.61 and 6.58 (AB, 4H, J=9 Hz, Ar—H), 3.76–3.66 (m, 2H, OCH2), 3.27 (q, J=3.0 Hz, 4H, 2NCH2), 3.33, 3.29, 3.07 and 3.03 (AB, J=12 Hz, 2H, CH2), 2.80–2.71 (m, 2H, CH2), 2.35 and 2.09 (m, 2H, CH2), 1.79 (m, H, CH), 1.04 (t, J=3.0 Hz, 6H, 2CH3), 0.84 (d, J=6.0 Hz, 6H, 2 CH3). MS (ESI) (M+1)+ 507, (M−1)+ 505.

Workup

  1. customAfter purging with nitrogen
  2. customThe reaction mixture was partitioned between methylene chloride and water
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on column of silica gel

Sources & evidence

ORD record
ord-facf37899fa24cd9ab0f554505af9cb8
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

Loading…