Benzo(b)thiophene, 3-bromo- → 1-[4-(1-Benzothien-3-ylamino)benzoyl]-N,N-dimethylpyrrolidin-3-amine

HRID 1176060

反応式

HRID 1176060 の反応式
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.Br[C:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21][CH:20]=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC(P(C(C)(C)C)[C]1[CH][CH][CH][CH]1)(C)C.C1C=CC([C]2[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C](C3C=CC=CC=3)[C]2C2C=CC=CC=2)=CC=1.[Fe]>[S:21]1[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:19]([NH:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([N:8]3[CH2:12][CH2:11][CH:10]([N:13]([CH3:14])[CH3:15])[CH2:9]3)=[O:7])=[CH:4][CH:3]=2)=[CH:20]1

参加物

6

反応物 3

HCID 123250Benzo(b)thiophene, 3-bromo-HCID 225674711-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidineHCID 23676156Sodium t-butoxide

生成物 1

HCID 247948791-[4-(1-Benzothien-3-ylamino)benzoyl]-N,N-dimethylpyrrolidin-3-amine収率 14.3%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 178454872HCID 178454872、化合物触媒

反応条件

温度
80 °C

実験手順

A mixture of 1-(4-aminobenzoyl)-3-dimethylamino-pyrrolidine (50 mg, 0.21 mmol), 3-bromobenzothiophene (50 mg, 0.23 mmol), sodium tert-butoxide (44 mg, 34 mmol), tris(dibenzylideneacetone)dipalladium(0) (3 mg, 0.002 mmol), CTC-Q-Phos (6 mg, 0.004 mmol) is heated to 80° C. for 16 h and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, methanol and water and purified by reverse-phase semi-preparative HPLC1 to give the title compound as a white powder (11 mg), identified by HPLC and mass spectral analyses. Retention Time, 2.62 min.; MS [366.2 m/e (M+H)]. 1Semi-preparative HPLC Conditions: A=0.02% TFA in water, B=0.02% TFA in acetonitrile, 10-95% B in 8 min., 34 mL/min, 50° C., 215 nm detection, Waters Xterra™ 20×50 mm column.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of DMSO, methanol and water
  3. custompurified by reverse-phase semi-preparative HPLC1

出典と根拠

ORDレコード
ord-836d361ff6cb4c1fb9960d8ed8864ed9
出典データセット
uspto-grants-2010_11
特許番号
US07842715B2

関連ノート

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