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

反応式

HRID 1434590 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 81531Diisopropylethylamine溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-7338ca25405f4cc3ae8e178f4bc53e3d
出典データセット
uspto-grants-2009_11
特許番号
US07615550B2

関連ノート

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