Water → HCID 67084397, compound

HRID 79087Notes

Reaction equation

HRID 79087 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])[C:13]([NH2:19])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:29]1([S:32](Cl)(=[O:34])=[O:33])[CH2:31][CH2:30]1.O.C(OCC)(=O)C>N1C=CC=CC=1.C1CCCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])[C:13]([NH:19][S:32]([CH:29]3[CH2:31][CH2:30]3)(=[O:34])=[O:33])=[C:14]([O:17][CH3:18])[CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2760919Cyclopropanesulfonyl chlorideHCID 67083628HCID 67083628, compound

Product 1

HCID 67084397HCID 67084397, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8078CyclohexaneSolvent

Procedure

To a solution of 5-amino-4-(2-fluoro-4-iodo-phenylamino)-6-methoxy-indazole-1-carboxylic acid tert-butyl ester (200 mg, 0.401 mmol) in pyridine (2 mL) was added cyclopropyl sulfonyl chloride (281 mg, 2.0 mmol) and the reaction mixture stirred at room temperature for 18 hours. The reaction mixture was treated with water and extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried (Na2SO4), filtered and concentrated in vacuo to give an oily residue. The residue was subjected to flash chromatography (Si—PPC, gradient 0 to 25% ethyl acetate in cyclohexane) to give the title compound as an off-white foam (217 mg, 89%). LCMS (Method B) RT=4.16 min, [M+H]+=603.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an oily residue

Sources & evidence

ORD record
ord-61d24130bf7f487c90c41e16bbcced81
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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