Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 25181625, compound

HRID 1510424Notes

Reaction equation

HRID 1510424 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([OH:16])=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[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.[NH2:41][C@@H:42]1[CH2:47][CH2:46][CH2:45][C@H:44]([OH:48])[CH2:43]1>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:14]([NH:41][C@@H:42]2[CH2:47][CH2:46][CH2:45][C@H:44]([OH:48])[CH2:43]2)=[O:16])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 25630532(1S,3R)-3-aminocyclohexanolHCID 671211334-Chloro-5-(4-chlorophenyl)isoxazole-3-carboxylic acid

Product 1

HCID 25181625HCID 25181625, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 18 mg (0.07 mmol) of 4-chloro-5-(4-chlorophenyl)isoxazole-3-carboxylic acid in anhydrous N,N-dimethylformamide (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 27 mg, 0.07 mmol), followed by (1S,3R)-3-aminocyclohexanol (8.1 mg, 0.07 mmol) with stirring at room temperature. After 18 h, the solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The aqueous layer was separated and repeatedly extracted with ethyl acetate, the combined organic extracts were dried (MgSO4), the solvent removed in vacuo and the residue was purified by preparative HPLC to afford the title compound: (5.3 mg, 0.015 mmol). MS (ESI) m/z (M+H+): 354.9/356.9.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionrepeatedly extracted with ethyl acetate
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cf5e3ebce42044799c40d8ef36190588
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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