Acetic Acid → HCID 131727929, compound

HRID 2242667Notes

Reaction equation

HRID 2242667 reaction equation
[F:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([C@@H:9]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C@H:10]([CH:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH3:19])[CH2:14][CH2:13]2)[CH3:11])=[O:8])[CH2:3]1.[C:28](O)(=[O:30])[CH3:29].C(N(CC)C(C)C)(C)C.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:23]([O:22][C:21](=[O:27])[NH:20][C@H:9]([C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([F:1])[CH2:3]1)=[O:8])[C@H:10]([CH:12]1[CH2:17][CH2:16][CH:15]([N:18]([C:28](=[O:30])[CH3:29])[CH3:19])[CH2:14][CH2:13]1)[CH3:11])([CH3:26])([CH3:25])[CH3:24]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86761061HCID 86761061, compound

Product 1

HCID 131727929HCID 131727929, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the material prepared in Step C (0.020 g, 0.052 mmol) in DMF (1 mL) was added acetic acid (0.003 mL, 0.06 mmol), N,N-diisopropylethylamine (0.045 mL, 0.26 mmol), HOAT (0.095 mL of a 0.6 M DMF solution, 0.095 mmol), and HATU (0.022 g, 0.095 mmol). After 3 h at ambient temperature the reaction was diluted with 100 mL of ethyl acetate and washed with 0.5 M aqueous sodium bicarbonate. The organic layer was washed with brine, dried (magnesium sulfate), and concentrated in vacuo. Purification by reverse phase liquid chromatography (20%-60% acetonitrile in water gradient) afforded the title compound as a white solid. LC/MS 450.3 (M+Na).

Workup

  1. washwashed with 0.5 M aqueous sodium bicarbonate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customPurification by reverse phase liquid chromatography (20%-60% acetonitrile in water gradient)

Sources & evidence

ORD record
ord-a82fd70400da4907adcdd75fd00ed919
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

Loading…