Triethylamine → 6-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 1677707Notes

Reaction equation

HRID 1677707 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([OH:20])=O)[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:9]=2[CH:10]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:61][CH2:62][C:63]1[CH:68]=[CH:67][C:66]([S:69]([NH:72][CH3:73])(=[O:71])=[O:70])=[CH:65][CH:64]=1>CN(C=O)C>[CH3:73][NH:72][S:69]([C:66]1[CH:67]=[CH:68][C:63]([CH2:62][NH:61][C:18]([C:4]2[C:5]3[CH:6]=[N:7][N:8]([C:11]4[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=4)[C:9]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)=[O:20])=[CH:64][CH:65]=1)(=[O:70])=[O:71]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 164609784-(Aminomethyl)-N-methylbenzene-1-sulfonamideHCID 581389136-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Product 1

HCID 444698036-Bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred room temperature solution of 6-bromo-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.25 g, 0.70 mmol) in DMF (15 mL) was added PyBOP (0.45 g, 0.90 mmol) and triethylamine (0.20 g, 1.6 mmol). After 15 minutes, 4-aminomethyl-N-methyl-benzenesulfonamide (0.15 g, 0.7 mmol) was added. After 5 hours, the reaction was quenched with water (30 mL), and extracted with ethyl acetate (30 mL). The combined organic layers were washed with brine (30 mL) and dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 30-50% ethyl acetate in hexanes to afford the title compound.

Workup

  1. waitAfter 5 hours
  2. customthe reaction was quenched with water (30 mL)
  3. extractionextracted with ethyl acetate (30 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with a gradient of 30-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e7cf63019dfc4d7491b6ce5c7d77d417
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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