3-(Methoxymethyl)benzeneboronic acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-5-{3-[(methyloxy)methyl]phenyl}-2-thiophenesulfonamide

HRID 130457

反応式

HRID 130457 の反応式
Br[C:2]1[S:6][C:5]([S:7]([NH:10][C:11]2[CH:16]=[C:15]([N:17]3[CH2:22][C@H:21]([CH3:23])[NH:20][C@H:19]([CH3:24])[CH2:18]3)[CH:14]=[CH:13][C:12]=2[O:25][CH3:26])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH3:27][O:28][CH2:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.CC(C)([O-])C.[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][C@H:19]1[NH:20][C@@H:21]([CH3:23])[CH2:22][N:17]([C:15]2[CH:14]=[CH:13][C:12]([O:25][CH3:26])=[C:11]([NH:10][S:7]([C:5]3[S:6][C:2]([C:34]4[CH:33]=[CH:32][CH:31]=[C:30]([CH2:29][O:28][CH3:27])[CH:35]=4)=[CH:3][CH:4]=3)(=[O:9])=[O:8])[CH:16]=2)[CH2:18]1

参加物

7

反応物 3

HCID 38258553-(Methoxymethyl)benzeneboronic acidHCID 23665647Potassium tert-butoxideHCID 590070585-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide

生成物 1

HCID 59007093N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-5-{3-[(methyloxy)methyl]phenyl}-2-thiophenesulfonamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 5-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-2-thiophenesulfonamide (E122) (100 mg, 0.22 mmol) and {3-[(methyloxy)methyl]phenyl}boronic acid (83 mg, 0.5 mmol) in DME (3 ml) was added potassium tert-butoxide (210 mg, 1.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (15 mg, 0.013 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The resulting mixture was then concentrated in Genevac and residues passed over SCX. Basic fractions were re-concentrated in Genevac and the residue purified using mass directed autoprep HPLC to afford the title compound (E123). MS (ES+) m/e 502 [M+H]+.

後処理

  1. concentrationThe resulting mixture was then concentrated in Genevac and residues
  2. concentrationBasic fractions were re-concentrated in Genevac
  3. customthe residue purified

出典と根拠

ORDレコード
ord-4c6e2ccf7dda44938fab0b983311ce43
出典データセット
uspto-grants-2008_06
特許番号
US07381728B2

関連ノート

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