Dimethylformamide → HCID 67448799, compound

HRID 1625716Notes

Reaction equation

HRID 1625716 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([O-:12])=O)=[CH:6][C:5]=1[NH2:15])(=[O:3])[CH3:2].[Li+].CN(C([O:24][N:25]1N=N[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C=[O:45])C.CC[N:48]([CH:52](C)C)C(C)C>CCOC(C)=O>[C:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][C:10]([NH:48][CH2:52][C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:25]([O-:24])=[O:45])[CH:31]=2)=[O:12])=[CH:6][C:5]=1[NH2:15])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58481104HCID 58481104, compound

Product 1

HCID 67448799HCID 67448799, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Lithium 2-(4-acetyl-3-aminophenoxy)acetate (215 mg), HBTU (379 mg), and 10 mL DMF were combined in a 20 mL glass vial and the resulting slurry was stirred at ambient temperature for 1 hour at which time the reaction mixture became almost homogeneous. To the vial, then, were added 3′-nitrobenzylamine HCl (192 mg) and DIEA (191 μL), and the reaction was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with EtOAc, washed successively with water, sat aq. NaCl, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel flash chromatography (hexanes/EtOAc), affording the title compound as a yellow solid. MS (ESI+): m/z 344.10 (MH+). H-NMR (400 MHz, CDCl3): 2.526 (3H, 3), 4.587 (2H, s), 4.641 (2H, d, J=6.4 Hz), 6.091 (1H, d, J=2.8 Hz), 6.239 (1H, dd, J=2.8 Hz, 8.8 Hz), 6.969 (1H, br.s), 7.511 (1H, t, J=7.6 Hz), 7.624 (1H, d, J=7.6 Hz), 7.678 (1H, d, J=8.8 Hz), 7.849 (1H, m), 8.131 (1H, s), 8.141 (1H, d, J=7.6 hz).

Workup

  1. stirringthe reaction was stirred at ambient temperature for 30 minutes
  2. washwashed successively with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel flash chromatography (hexanes/EtOAc)

Sources & evidence

ORD record
ord-1208b5d651a148a8bb33f596cad74378
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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