4-(Trifluoromethoxy)benzoic acid → HCID 131727927, compound

HRID 2242663Notes

Reaction equation

HRID 2242663 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)=[O:19])[C@H:9]([CH:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]([F:40])([F:39])[O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.C1C=NC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.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:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:18]([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)=[O:19])[C@H:9]([CH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:34](=[O:35])[C:33]2[CH:37]=[CH:38][C:30]([O:29][C:28]([F:27])([F:39])[F:40])=[CH:31][CH:32]=2)[CH2:13][CH2:12]1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 676134-(Trifluoromethoxy)benzoic 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 131727924HCID 131727924, compound

Product 1

HCID 131727927HCID 131727927, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the material prepared in Step B of Example 24 (0.020 g, 0.054 mmol) in DMF (2 mL) was added 4-(trifluoromethoxy)benzoic acid (0.0090 g, 0.059 mmol), HOAT (0.0080 g, 0.059 mmol), N,N-diisopropylethylamine (0.047 mL, 0.27 mmol) and HATU (0.022 g, 0.059 mmol). After 24 h at ambient temperature the reaction was diluted with 100 mL of ethyl acetate and washed with 100 mL of 0.5 M aqueous sodium bicarbonate. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Purification by reverse phase HPLC (30%-60% acetonitrile in H20 gradient) afforded the title compound as a white solid. LC/MS 506.3 (M+1).

Workup

  1. washwashed with 100 mL of 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 HPLC (30%-60% acetonitrile in H20 gradient)

Sources & evidence

ORD record
ord-41b1da3bee544468b93c0617d28ff8ec
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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