O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 5-Fluoro-1-methyl-3-[(4-{4-[3-(2-methylpiperidin-1-yl)propoxy]phenyl}piperazin-1-yl)carbonyl]-1H-indole

HRID 1434590

반응식

HRID 1434590 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]([OH:14])=O.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH3:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][N:39]1[CH2:44][CH2:45][CH2:46][O:47][C:48]1[CH:53]=[CH:52][C:51]([N:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)=[CH:50][CH:49]=1>CN(C=O)C.C(N(C(C)C)CC)(C)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[C:12]([N:57]1[CH2:58][CH2:59][N:54]([C:51]2[CH:50]=[CH:49][C:48]([O:47][CH2:46][CH2:45][CH2:44][N:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH:38]3[CH3:37])=[CH:53][CH:52]=2)[CH2:55][CH2:56]1)=[O:14]

참가 물질

6

반응물 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 183851025-fluoro-1-methyl-1H-indole-3-carboxylic acidHCID 579358411-{4-[3-(2-Methylpiperidin-1-yl)propoxy]phenyl}piperazine

생성물 1

HCID 579357735-Fluoro-1-methyl-3-[(4-{4-[3-(2-methylpiperidin-1-yl)propoxy]phenyl}piperazin-1-yl)carbonyl]-1H-indole수율 45.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 81531Diisopropylethylamine용매

실험 절차

A solution of 5-fluoro-1-methyl-1H-indole-3-carboxylic acid (19.3 mg) and O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) (56 mg) in DMF (1 ml) and diisopropylethylamine (0.035 ml) was stirred for 10 min before 1-{4-[3-(2-methylpiperidin-1-yl)propoxy]phenyl}piperazine (E76b) (21.3 mg) in DMF (0.5 ml) was added. The mixture was stirred for 18 h and then concentrated under reduced pressure. The residue was purified by SPE ion exchange chromatography on an SCX-2 cartridge (1 g). The cartridge was washed with methanol (3 ml) and the product eluted with 2M ammonia in methanol (2.5 ml), to give the title compound (15 mg) LCMS RT=2.42 min, ES+ve m/z 493 (M+H)+.

후처리

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by SPE ion exchange chromatography on an SCX-2 cartridge (1 g)
  4. washThe cartridge was washed with methanol (3 ml)
  5. washthe product eluted with 2M ammonia in methanol (2.5 ml)

출처 및 근거

ORD 기록
ord-7338ca25405f4cc3ae8e178f4bc53e3d
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615550B2

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