Ethyl Acetate → HCID 60141904, compound

HRID 2047240Notes

Reaction equation

HRID 2047240 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:25])([F:24])[F:23])[O:11][N:10]=1.[CH3:33][NH:34][O:35][CH3:36].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OC(=O)C)C>CN(C)O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([N:34]([O:35][CH3:36])[CH3:33])=[O:16])=[C:12]([C:17]2[CH:18]=[N:19][N:20]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=3)[C:21]=2[C:22]([F:24])([F:25])[F:23])[O:11][N:10]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14232N,O-DimethylhydroxylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86668506HCID 86668506, compound

Product 1

HCID 60141904HCID 60141904, compound

Reagents, catalysts & solvents 1

HCID 27970DimethylhydroxylamineSolvent

Procedure

To a solution of 10.8 g (22.2 mmol) 3-(2-chloro-6-fluorophenyl)-5-(1-(3-chlorophenyl)-5-(trifluoromethyl)-1H-pyrazol-4-yl)isoxazole-4-carboxylic acid, 2.17 g (1 eq) N,O-Dimethylhydroxylamine and 8.42 g (1 eq) HBTU in dimethylhydroxylamine 3.68 mL DIPEA were added. The mixture was stirred overnight at r.t. The solvent was removed in the vacuum. The residue was resolved in ethylacetate and extracted with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq). The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed in the vacuum. TLC (6:4 petrolether:ethylacetate) showed residual educt. The product was isolated by column chromatoghraphy (6:4) petrolether:ethylacetate). The product (example 63) was dried under vacuum to yield 2.28 g (19%). Result of LC/MS MH+: 528.8; 1H NMR (DMSO-d6; CCl4): 3.08 (3H, s, CH3), 3.36 (3H, s, CH3), 7.40-7.81 (7H, m, CH-arom.), 8.39 (1H, s, CH-pyraz.)

Workup

  1. customThe solvent was removed in the vacuum
  2. extractionextracted with sodium hydrogen carbonate (5%, aq) and citric acid (5%, aq)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed in the vacuum
  5. customThe product was isolated by column chromatoghraphy (6:4) petrolether
  6. customThe product (example 63) was dried under vacuum
  7. customto yield 2.28 g (19%)
  8. customResult of LC/MS MH+

Sources & evidence

ORD record
ord-191818433fa84695bbae671d36c3b6d2
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

Loading…