Hydrochloric Acid → HCID 57618438, compound

HRID 1873998Notes

Reaction equation

HRID 1873998 reaction equation
[CH3:1][NH:2][CH2:3][CH3:4].[B:5]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[C:10]([F:17])[CH:9]=1)([OH:7])[OH:6].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH4+].[Cl-].Cl>O.CN(C=O)C>[CH2:3]([N:2]([CH3:1])[C:12]([C:11]1[CH:15]=[CH:16][C:8]([B:5]([OH:6])[OH:7])=[CH:9][C:10]=1[F:17])=[O:14])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 12219N-MethylethylamineHCID 25517Ammonium ChlorideHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57618438HCID 57618438, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

N-Methylethanamine (1.5 mL, 17.46 mmol) was added to a DMF (10 mL) solution (sonicated to help dissolve) of 4-borono-2-fluorobenzoic acid (1.13 g, 6.14 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (2.54 g, 6.68 mmol). After 3 h at room temperature, saturated NH4Cl (50 mL) and water (10 mL) were added. The mixture was acidified to pH 3 with concentrated HCl (˜0.5 mL). The mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine (5 mL), dried (MgSO4) and concentrated to give a thick brown oil, which was treated with water (7 mL) and allowed to stand overnight. The white needles were removed by filtration. The filtrate was purified by reverse phase HPLC (Sunfire S10 30×250 mm column, 30-50% solvent B gradient) to give the expected product as white glassy solid (1.1036 g, 80% yield). LC retention time: 2.49 min (analytical HPLC Method A).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with brine (5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a thick brown oil, which
  6. waitto stand overnight
  7. customThe white needles were removed by filtration
  8. customThe filtrate was purified by reverse phase HPLC (Sunfire S10 30×250 mm column, 30-50% solvent B gradient)

Sources & evidence

ORD record
ord-272900cdde6a4e148a0fafb6c76d88ed
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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