Triethylamine → HCID 178477692, compound

HRID 1888227Notes

Reaction equation

HRID 1888227 reaction equation
Cl.[C:2]1([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][N:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:33]([S:35]([N:23]1[CH2:24][CH2:25][CH:20]([C:11]2[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=[C:8]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:9]=3)[NH:13][N:12]=2)[CH2:21][CH2:22]1)(=[O:37])=[O:36])[CH3:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 1784795395-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride

Product 1

HCID 178477692HCID 178477692, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

The crude 5-phenyl-3-(4-piperidinyl)-1H-indazole-7-carboxamide hydrochloride (Example 2) was suspended in DMF (8 mL) and treated with triethylamine (0.3 mL, 2.2 mmols), DMAP (0.0056 g, 0.065 mmol), and ethane sulfonyl chloride (0.044 mL, 0.47 mmols) at ambient temperature. After 12 hrs, the mixture was concentrated to dryness in vacuo at ambient temperature, treated with water (10 mL), and extracted with ethyl acetate (3×25 mL). The organic phase was washed with water, dried over MgSO4, filtered, and concentrated to give a light brown solid. This was purified via preparative HPL, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) to give 0.080 g of a white solid.

Workup

  1. concentrationthe mixture was concentrated to dryness in vacuo at ambient temperature
  2. additiontreated with water (10 mL)
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe organic phase was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light brown solid
  9. customThis was purified via preparative HPL
  10. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-de586e724b384926b92d6f4592cff8a5
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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