1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine → 1,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamide

HRID 244689Notes

Reaction equation

HRID 244689 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([C:8](Cl)=[O:9])=[N:3]1.[C:11]1([S:17]([N:20]2[C:28]3[CH:27]=[C:26]([Sn:29]([CH3:32])([CH3:31])[CH3:30])[CH:25]=[C:24]([NH2:33])[C:23]=3[CH:22]=[N:21]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([CH3:7])[C:4]([C:8]([NH:33][C:24]2[CH:25]=[C:26]([Sn:29]([CH3:32])([CH3:31])[CH3:30])[CH:27]=[C:28]3[C:23]=2[CH:22]=[N:21][N:20]3[S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[O:9])=[N:3]1

Participants

5

Reactant 2

HCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine2×HCID 583563801,4-Dimethyl-1H-pyrazole-3-carbonyl chloride2×

Product 1

HCID 583564471,4-Dimethyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent4×

Procedure

1,4-Dimethyl-1H-pyrazole-3-carbonyl chloride (46 mg) in DCM (2.5 ml) was added over 5 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (100 mg) in DCM (2.5 ml) and pyridine (0.023 ml). The reaction was stirred at room temperature for 2 h. Separately, 1,4-dimethyl-1H-pyrazole-3-carbonyl chloride (273 mg) in DCM (5 ml) was added over 10 min to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (600 mg) in DCM (25 ml) and pyridine (0.2 ml). The reaction was stirred at room temperature for 1 h. The reactions were combined and separated between saturated sodium bicarbonate (aq) and DCM. The DCM was passed through a hydrophobic frit then dried. The residue was dissolved in DCM and purified using a silica cartridge, preconditioned with cyclohexane. The cartridge was eluted with cyclohexane:diethyl ether (1:1, v/v) then diethyl ether, then 10% methanol in diethyl ether and finally with 50% methanol in diethyl ether. Pure fractions were combined and dried to give title compound, 753 mg.

Workup

  1. stirringThe reaction was stirred at room temperature for 1 h
  2. customseparated between saturated sodium bicarbonate (aq) and DCM
  3. customthen dried
  4. dissolutionThe residue was dissolved in DCM
  5. custompurified
  6. washThe cartridge was eluted with cyclohexane:diethyl ether (1:1
  7. customdried

Sources & evidence

ORD record
ord-c65afc6317e64831a003cef75c706700
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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