Triethylamine → 6-Cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-(1-methyl-piperidin-4-ylsulfamoyl)-benzylamide

HRID 1677717Notes

Reaction equation

HRID 1677717 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:19]([OH:21])=O)[C:6]2[CH:7]=[N:8][N:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:10]=2[CH:11]=1)#[N:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:62][CH2:63][C:64]1[CH:69]=[CH:68][C:67]([S:70]([NH:73][CH:74]2[CH2:79][CH2:78][N:77]([CH3:80])[CH2:76][CH2:75]2)(=[O:72])=[O:71])=[CH:66][CH:65]=1>CN(C=O)C.O.C(OCC)(=O)C>[CH3:80][N:77]1[CH2:76][CH2:75][CH:74]([NH:73][S:70]([C:67]2[CH:68]=[CH:69][C:64]([CH2:63][NH:62][C:19]([C:5]3[C:6]4[CH:7]=[N:8][N:9]([C:12]5[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=5)[C:10]=4[CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)=[O:21])=[CH:65][CH:66]=2)(=[O:72])=[O:71])[CH2:79][CH2:78]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 433735484-(Aminomethyl)-N-(1-methylpiperidin-4-yl)benzenesulfonamideHCID 581389176-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid

Product 1

HCID 581387966-Cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-(1-methyl-piperidin-4-ylsulfamoyl)-benzylamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 6-cyano-1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (0.040 g, 0.14 mmol) in DMF (15 mL) was added PyBOP (0.1 g, 0.2 mmol) and triethylamine (0.04 g, 0.3 mmol) at room temperature. After 15 minutes, 4-aminomethyl-N-(1-methyl-piperidin-4-yl)-benzenesulfonamide (0.05 g, 0.16 mmol) was added. After 5 hours, the mixture was diluted with water (30 mL) and ethyl acetate (30 mL). The organic layer separated and washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated. 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 organic layer separated
  3. washwashed with brine (20 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  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-ecdf4f28b65f4bb28d33767e9c35b5f5
Source dataset
uspto-grants-2011_08
Patent number
US08008327B2

Reaction notes

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