Water → benzyl 4-{[(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)amino]sulfonyl}-1-piperidinecarboxylate

HRID 1269771Notes

Reaction equation

HRID 1269771 reaction equation
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([NH2:23])=[CH:20][CH:21]=2)[CH:16]=[N:15]1.Cl[S:25]([CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:30][CH2:29]1)(=[O:27])=[O:26].O>C(Cl)Cl>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[N:14]1[C:22]2[C:17](=[CH:18][C:19]([NH:23][S:25]([CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[O:35])[CH2:32][CH2:33]3)(=[O:26])=[O:27])=[CH:20][CH:21]=2)[CH:16]=[N:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21931260Benzyl 4-(chlorosulfonyl)piperidine-1-carboxylateHCID 229339271-(Oxan-2-yl)-1H-indazol-5-amine

Product 1

HCID 69431167benzyl 4-{[(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)amino]sulfonyl}-1-piperidinecarboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.789 ml, 5.69 mmol) was added to a solution of 1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (1.04 g, 4.79 mmol) and benzyl 4-(chlorosulfonyl)-1-piperidinecarboxylate (1.5 g, 4.74 mmol) in methylene chloride (50 ml) at 0° C. and stirred at 0° C. for 30 minutes and then at room temperature for 15 hours. The reaction solution was poured into water and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate=3/1) to obtain benzyl 4-{[(1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-yl)amino]sulfonyl}-1-piperidinecarboxylate (1.32 g, 56%).

Workup

  1. waitat room temperature for 15 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-69bb021a76854a3eaa06f7c87a4a1d13
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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