Cyclopropanesulfonyl chloride → HCID 67083644, compound

HRID 79085Notes

Reaction equation

HRID 79085 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=3[F:26])[C:13]([NH2:17])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:27]1([S:30](Cl)(=[O:32])=[O:31])[CH2:29][CH2:28]1>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([I:25])=[CH:21][C:20]=3[F:26])[C:13]([NH:17][S:30]([CH:27]3[CH2:29][CH2:28]3)(=[O:32])=[O:31])=[CH:14][CH:15]=2)[CH:10]=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2760919Cyclopropanesulfonyl chlorideHCID 67083692HCID 67083692, compound

Product 1

HCID 67083644HCID 67083644, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-amino-4-(2-fluoro-4-iodo-phenylamino)-indazole-1-carboxylic acid tert-butyl ester (200 mg, 0.43 mmol) in pyridine (2 mL) was added cyclopropyl sulfonyl chloride (0.218 mL, 2.14 mmol) and the mixture stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, washed with brine, then dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 10-35% ethyl acetate in cyclohexane) to yield the title compound (206 mg, 84%). LCMS (Method B): RT=4.17 min, [MH]+=573.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93f8818234754a25a271a00bf7e42fa7
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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