Dimethylformamide → HCID 90411297, compound

HRID 1754617Notes

Reaction equation

HRID 1754617 reaction equation
C([Si](C)(C)[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[N:22][C:21]1=[O:27])[C@H:9]([O:11][Si](C(C)(C)C)(C)C)[CH3:10])(C)(C)C.CN(C=O)C.C(OC(=O)C)(=O)C>C(N(CC)CC)C>[NH2:26][C:23]1[CH:24]=[CH:25][N:20]([CH2:19][C@H:8]([C@H:9]([OH:11])[CH3:10])[CH2:7][OH:6])[C:21](=[O:27])[N:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 90411860HCID 90411860, compound

Product 1

HCID 90411297HCID 90411297, compoundYield 225.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 44 (1.2 g. 2.7 mmol) in 15 of anhydrous DMF was added triethylamine (0.45 ml) followed by 0.31 ml (3.3 mmol) of acetic anhydride. The reaction was kept at room temperature for 1 day, then 3 hrs at 50 C and concentrated. The oily residue was dried by co-evaporation with xylene and then re-dissolved in ethyl acetate. The solution was washed with saturated NaHCO3 (2×100 ml), saturated NaCl, dried over MgSO4. Concentration of the extract and drying in vacuo afforded 1.3 g (99%) of 45 as an off-white amorphous solid. 1H NMR (DMSO-d6): δ 10.79 (s, 1H), 7.94 (d, J=7 Hz, 1H), 7.12 (d, J=7 Hz, 1H), 4.01 (m, 1H), 3.87 (m, 1H), 3.69 (m, 1H), 3.56 (d, J=6 Hz, 2H), 2.14 (m, 1H), 2.08 (s, 3H), 1.14 (d, J=6 Hz, 3H), 0.84 (s, 9H), 0.82 (s, 9H), 0.02 (s, 6H), −0.02 (s, 3H), −0.03 (s, 3H).

Workup

  1. concentration3 hrs at 50 C and concentrated
  2. dry with materialThe oily residue was dried by co-evaporation with xylene
  3. dissolutionre-dissolved in ethyl acetate
  4. washThe solution was washed with saturated NaHCO3 (2×100 ml), saturated NaCl
  5. dry with materialdried over MgSO4
  6. extractionConcentration of the extract
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-85be6c4f8aeb469285bbab32ac500a41
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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