Piperidine → HCID 11569170, compound

HRID 20566Notes

Reaction equation

HRID 20566 reaction equation
CCN(C(C)C)C(C)C.[OH:10][CH2:11][C@H:12]([CH3:39])[O:13][C:14]1[CH:15]=[C:16]([CH:27]=[C:28]([C:30]([NH:32][C:33]2[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=2)=[O:31])[CH:29]=1)[O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1.CN(C(ON1N=N[C:50]2[CH:51]=[CH:52][CH:53]=[N:54][C:49]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C>[OH:10][CH2:11][C@H:12]([CH3:39])[O:13][C:14]1[CH:29]=[C:28]([CH:27]=[C:16]([O:17][C:18]2[CH:26]=[CH:25][C:21]([C:22]([N:54]3[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]3)=[O:24])=[CH:20][CH:19]=2)[CH:15]=1)[C:30]([NH:32][C:33]1[CH:37]=[CH:36][N:35]([CH3:38])[N:34]=1)=[O:31]

Participants

6

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 593468664-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

Product 1

HCID 11569170HCID 11569170, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.36 mL, 1.95 mmol) was added to a suspension of 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid (200 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. The solvent was evaporated. Water (30 mL) was added and the mixture extracted with ethyl acetate (3×15 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 (167 mg).

Workup

  1. customThe solvent was evaporated
  2. additionWater (30 mL) was added
  3. extractionthe mixture extracted with ethyl acetate (3×15 mL)
  4. washThe combined organic extracts were washed with brine (30 mL)
  5. dry with materialdried, (MgSO4),
  6. customevaporated to a residue which
  7. customwas chromatographed on silica
  8. washeluting with a gradient of 0-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-25a3926d96164bfebece30f1aa4f3196
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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