Triethylamine → 1-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

HRID 1677682Notes

Reaction equation

HRID 1677682 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([OH:19])=O)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:60][CH2:61][C:62]1[CH:67]=[CH:66][C:65]([S:68]([NH:71][CH3:72])(=[O:70])=[O:69])=[CH:64][CH:63]=1>CN(C=O)C>[CH3:72][NH:71][S:68]([C:65]1[CH:66]=[CH:67][C:62]([CH2:61][NH:60][C:17]([C:12]2[C:11]3[CH:10]=[N:9][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:19])=[CH:63][CH:64]=1)(=[O:69])=[O:70]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 164609784-(Aminomethyl)-N-methylbenzene-1-sulfonamideHCID 581387741-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Product 1

HCID 581387891-(4-Fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-methylsulfamoyl-benzylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.05 g, 0.2 mmol) in DMF (10 mL) was added PyBOP (0.14 g, 0.30 mmol) and triethylamine (0.07 g, 0.6 mmol) at room temperature. After 15 minutes, 4-aminomethyl-N-methyl-benzenesulfonamide (0.04 g, 0.2 mmol) was added. After 5 hours, the mixture was quenched with water (30 mL) and diluted with ethyl acetate (30 mL). The organic layer was separated, washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes to afford the title compound.

Workup

  1. waitAfter 5 hours
  2. customthe mixture was quenched with water (30 mL)
  3. additiondiluted with ethyl acetate (30 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-33a84968e27f4201b0b630dc6b96bf1d
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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