Piperidine → HCID 11705955, compound

HRID 20569Notes

Reaction equation

HRID 20569 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([C:27]([NH:29][C:30]2[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=2)=[O:28])[CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:14]([OH:16])=O.CN(C(ON1N=N[C:51]2[CH:52]=[CH:53][CH:54]=[N:55][C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.O>[F:10][C:11]1[CH:12]=[C:13]([C:14]([N:55]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)=[O:16])[CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:27]([NH:29][C:30]1[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=1)=[O:28]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593469353-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

Product 1

HCID 11705955HCID 11705955, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.36 mL, 1.95 mmol) was added to a suspension of 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid (209 mg, 0.49 mmol), HATU (390 mg, 1.02 mmol) and piperidine (0.19 mL, 1.95 mmol) in DMF (3 mL), and the mixture stirred at ambient temperature for 24 hours. Water (30 mL) was added and the mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-20% methanol in ethyl acetate, to give the desired compound (116 mg).

Workup

  1. extractionthe mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas chromatographed on silica
  6. washeluting with a gradient of 0-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-d5344cbb75354419b82a61858da94bef
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

Loading…