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

HRID 1677682노트

반응식

HRID 1677682 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-33a84968e27f4201b0b630dc6b96bf1d
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008327B2

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