Triethylamine → HCID 25182304, compound

HRID 1510453Notes

Reaction equation

HRID 1510453 reaction equation
[Cl:1][C:2]1[C:3]([C:18](O)=[O:19])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[C:9]([F:17])[CH:8]=1.[O:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl.C(OC(=O)C)C>[Cl:1][C:2]1[C:3]([C:18]([NH:27][CH:24]2[CH2:25][CH2:26][O:21][CH2:22][CH2:23]2)=[O:19])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:14])[F:15])=[C:9]([F:17])[CH:8]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 4192234-AminotetrahydropyranHCID 67121150HCID 67121150, compound

Product 1

HCID 25182304HCID 25182304, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-chloro-5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid (45 mg, 0.145 mmol), tetrahydro-2H-pyran-4-amine (14.7 mg, 0.15 mmol) and triethylamine (61.3 μl, 0.44 mmol) in dichloromethane (2 mL) a 50 wt % solution of 1-propanephosphonic acid cyclic anhydride (64.9 μl, 0.22 mmol) in ethylacetate was added. After stirring for 1 hr, the reaction mixture was diluted with dichloromethane (10 mL) washed with NaHCO3 solution (10 mL) and concentrated in vacuo. The resulting residue was purified by silica gel chromatography, eluting with dichloromethane to 20% methanol in dichloromethane to afford the title compound: (18 mg, 0.046 mmol).

Workup

  1. washwashed with NaHCO3 solution (10 mL)
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with dichloromethane to 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-f7ba83d1c43a49f99d68b4ae094c58b9
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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