Dimethylformamide → HCID 86660605, compound

HRID 717633Notes

Reaction equation

HRID 717633 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].N1C(CN[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=2)=NN=N1.[CH3:36]N(C=O)C>>[CH2:28]([C:25]1[CH:24]=[CH:23][C:22]([CH2:36][N:6]2[CH2:5][CH2:4][N:3]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2]2=[O:1])=[CH:27][CH:26]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 68700715HCID 68700715, compoundHCID 178442648HCID 178442648, compound

Product 1

HCID 86660605HCID 86660605, compoundYield 16%

Procedure

To a solution of the product of Step A (0.03 g; 0.15 mmol) in anhydrous DMF (5 ml) 60% NaH in mineral oil (0.006 g; 0.15 mmol) was added at room temperature, under N2. After stirring for 1 h, the product of Example 4, Step B (0.042 g; 0.15 mmol) was added. The resulting mixture was stirred for additional 4 h and solvents were removed in vacuo. The residue was diluted to 10 ml with EtOAc, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.01 g; 16%) as a colourless solid. 1H-NMR (CDCl3) 7.16 (d, 2H, J=8.1 Hz); 7.11 (d, 3H, J=8.1 Hz); 4.34 (s, 2H); 3.95 (s, 2H); 3.4 (m, 2H); 3.21 (m, 2H); 2.56 (t, 3H, J=7.9 Hz); 1.65 (m, 2H); 1.43 (s, 9H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz).

Workup

  1. stirringThe resulting mixture was stirred for additional 4 h
  2. customsolvents were removed in vacuo
  3. additionThe residue was diluted to 10 ml with EtOAc
  4. washwashed with H2O, brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-b496befcba39489c8178b038e0ed9950
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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