Triethylamine → HCID 178523809, compound

HRID 1510456Notes

Reaction equation

HRID 1510456 reaction equation
[Cl:1][C:2]1[C:3]([C:17]([OH:19])=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.Cl.[NH2:45][C@@H:46]1[CH2:51][CH2:50][C@H:49]([OH:52])[CH2:48][CH2:47]1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:3]([C:17]([NH:45][C@H:46]2[CH2:51][CH2:50][C@@H:49]([OH:52])[CH2:48][CH2:47]2)=[O:19])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 671210774-Chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acidHCID 178479277HCID 178479277, compound

Product 1

HCID 178523809HCID 178523809, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred suspension of 4-chloro-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylic acid (50 mg, 0.17 mmol) in acetonitrile (2 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (85 mg, 0.22 mmol), followed by cis-4-aminocyclohexanol hydrochloride (26 mg, 0.17 mmol). Triethylamine (52 mg, 0.51 mmol) was added before heating in the microwave at 150° C. for 10 minutes. After 10 minutes, the solvent was removed in vacuo, and the residue was partitioned between water and dichloromethane. The aqueous layer was separated and extracted with dichloromethane (3×10 mL), the combined organic extracts were dried with MgSO4, filtered and the solvent removed in vacuo. The residue was purified by preparative HPLC to afford the title compound: (26 mg, 0.067 mmol).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between water and dichloromethane
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialthe combined organic extracts were dried with MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-2094fb9df2af47b6be95a6c4e99361c7
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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