Hydrochloric Acid → HCID 66691550, compound

HRID 520578Notes

Reaction equation

HRID 520578 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[C:9]1([S:15]([N:18]2[C:26]3[CH:25]=[C:24]([Sn:27]([CH3:30])([CH3:29])[CH3:28])[CH:23]=[C:22]([NH2:31])[C:21]=3[CH:20]=[N:19]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>N1C=CC=CC=1>[C:9]1([S:15]([N:18]2[C:26]3[C:21](=[C:22]([NH:31][C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)=[O:7])[CH:23]=[C:24]([Sn:27]([CH3:29])([CH3:28])[CH3:30])[CH:25]=3)[CH:20]=[N:19]2)(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682422-Furancarbonyl chlorideHCID 582557431-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine

Product 1

HCID 66691550HCID 66691550, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Furancarbonyl chloride (0.199 ml) was added to a stirred solution of 1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-amine (580 mg) in pyridine (10 ml) at RT. The mixture was stirred for 1 h. After this time, the mixture was acidified with 5 N HCl and extracted into ether (2×40 ml). The combined extracts were washed with aq sodium bicarbonate (20 ml), water (50 ml), dried (frit) and evaporated to dryness. The residual oil was purified on a 20 g Si isolute cartridge using ether as the eluent. The appropriate fractions were evaporated to give the title compound, 510 mg as a colourless solid.

Workup

  1. extractionextracted into ether (2×40 ml)
  2. washThe combined extracts were washed with aq sodium bicarbonate (20 ml), water (50 ml)
  3. customdried (frit)
  4. customevaporated to dryness
  5. customThe residual oil was purified on a 20 g Si
  6. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-dce525daf41542a0a539903d35cce0bf
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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