Sodium Bicarbonate → HCID 58356336, compound

HRID 244686Notes

Reaction equation

HRID 244686 reaction equation
[CH3:1][CH:2]([N:4]1[C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=[N:5]1)[CH3:3].[C:12]1([S:18]([N:21]2[C:29]3[CH:28]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:26]=[C:25]([NH2:34])[C:24]=3[CH:23]=[N:22]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.N1C=CC=CC=1>[CH3:1][CH:2]([N:4]1[C:8]([C:9]([NH:34][C:25]2[CH:26]=[C:27]([Sn:30]([CH3:33])([CH3:32])[CH3:31])[CH:28]=[C:29]3[C:24]=2[CH:23]=[N:22][N:21]3[S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])=[O:10])=[CH:7][CH:6]=[N:5]1)[CH3:3]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amineHCID 583564221-Isopropyl-1H-pyrazole-5-carbonyl chloride2×

Product 1

HCID 58356336HCID 58356336, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×

Procedure

1-(1-Methylethyl)-1H-pyrazole-5-carbonyl chloride (152 mg) in DCM (10 ml) was added dropwise to 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (350 mg) in DCM (15 ml) and pyridine (0.07 ml). The reaction was stirred at room temperature for 10 min before addition of further 1-(1-methylethyl)-1H-pyrazole-5-carbonyl chloride (10 mg). The reaction was stirred for 30 min, saturated sodium bicarbonate (aq) (25 ml) was added and stirred vigorously for 10 min before the DCM was separated through a hydrophobic frit and evaporated to dryness. The residue was dissolved in DCM and loaded onto a silica cartridge preconditioned with cyclohexane. The cartridge was eluted with 0-100% ether in cyclohexane. The compound containing fraction was evaporated to dryness to give title compound, 360 mg.

Workup

  1. customwas separated through a hydrophobic frit
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in DCM
  4. washThe cartridge was eluted with 0-100% ether in cyclohexane
  5. additionThe compound containing fraction
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-5adf37c1a544439baee1746721f3088d
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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