Dimethylformamide → HCID 86658642, compound

HRID 1625717Notes

Reaction equation

HRID 1625717 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH:13]=[O:14])[O:5][CH2:6][C:7]([O-:9])=O.[Li+].CN(C([O:23][N:24]1N=N[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:42]([CH:46](C)C)C(C)C.CN(C=[O:53])C>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH:13]=[O:14])[O:5][CH2:6][C:7]([NH:42][CH2:46][C:28]1[CH:27]=[CH:26][C:25]([N+:24]([O-:23])=[O:53])=[CH:30][CH:29]=1)=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58481140HCID 58481140, compound

Product 1

HCID 86658642HCID 86658642, compound

Procedure

Lithium 2-(3-amino-4-formylphenoxy)acetate (44.2 mg) and HBTU (79.6 mg) were put in a 20 mL glass vial and dry DMF (5 mL) was added. The resulting slurry was stirred at ambient temperature, which turned homogeneous within 10 minutes. After 15 min DIEA (50 μL) and 4′-nitrobenzylamine HCl (37.7 mg) were added to the reaction mixture, and the reaction was stirred at ambient temperature. After 30 minutes LC-MS analysis revealed a complete reaction. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed successively with dil. aq. citric acid, sat. aq. NaHCO3, and sat. aq. NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure, affording the title compound as a tan solid. MS (ESI+): m/z 330.10 (MH+). H-NMR (400 MHz, DMSO-d6): 4.463 (2H, d, J=6.0 Hz), 4.597 (2H, s), 6.246 (1H, d, J=2.4 hz), 6.308 (1H, dd, J=2.4 Hz, 8.8 Hz), 7.235 (1H, br.s), 7.465 (1H, d, 8.8 Hz), 7.518 (2H, d, J=8.8 Hz), 8.173 (2H, d, J=8.8 Hz), 8.821 (1H, t, J=6.2 Hz), 9.657 (1H, s). C-NMR (400 MHz, DMSO-d6): 41.415, 66.627, 98.724, 104.297, 113.217, 123.267, 128.056, 137.581, 146.303, 147.287, 152.698, 162.872, 167.526, 191.685.

Workup

  1. stirringthe reaction was stirred at ambient temperature
  2. waitAfter 30 minutes LC-MS analysis revealed
  3. customa complete reaction
  4. customThe reaction mixture was partitioned between EtOAc and water
  5. customThe organic layer was separated
  6. washwashed successively with dil. aq. citric acid, sat. aq. NaHCO3, and sat. aq. NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38e4516a0bf64cd29157ccd3da637764
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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