Triethylamine → HCID 66772122、化合物

HRID 1645354

反応式

HRID 1645354 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.C(Cl)(=O)C([Cl:17])=O.[CH2:20]([O:22][C:23]([N:25]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][N:32]=2)[CH2:26]1)=[O:24])[CH3:21].C(N(CC)CC)C>ClCCl.CN(C=O)C>[ClH:17].[CH2:20]([O:22][C:23]([N:25]1[CH2:29][CH2:28][C@H:27]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:10]([C:8]3[S:9][C:5]4[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][C:6]=4[CH:7]=3)=[O:12])=[CH:33][N:32]=2)[CH2:26]1)=[O:24])[CH3:21]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 7377375-Bromo-benzo(b)thiophene-2-carboxylic acidHCID 59365133HCID 59365133、化合物

生成物 1

HCID 66772122HCID 66772122、化合物収率 48.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 5-bromobenzothiophene-2-carboxylic acid (109 mg, 0.42 mmol) in dichloromethane (5 mL) was added oxalyl chloride (2M in dichloromethane, 0.5 mL) and one drop of DMF. The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was diluted with benzene (10 mL) and then concentrated to dryness. The residue was dissolved in dichloromethane (5 mL) and treated with (S)-3-(5-amino-pyridin-2-ylamino)-pyrrolidine-1-carboxylic acid ethyl ester (106 mg, 0.42 mmol) in dichloromethane (5 mL) containing triethylamine (0.1 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with ethyl acetate and saturated ammonium chloride solution. Organic layer was washed with brine and dried over sodium sulfate. Solvents were evaporated and the residue was treated with methanol (1 mL) and hydrogen chloride in ether. Solvents were evaporated and the residue was treated with ether. The precipitate was filtered and washed with ether to give a light pink solid as (S)-3-{5-[(5-bromo-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-ylamino}-pyrrolidine-1-carboxylic acid ethyl ester hydrochloride (100 mg, 48.3% yield). LCMS for C21H21BrN4O3S calcd. (m/e) 488, observed 489 (M+H).

後処理

  1. customsolvents were evaporated
  2. additionThe residue was diluted with benzene (10 mL)
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane (5 mL)
  5. stirringThe mixture was stirred at room temperature for 1 hr
  6. customsolvents were evaporated
  7. extractionThe residue was extracted with ethyl acetate and saturated ammonium chloride solution
  8. washOrganic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customSolvents were evaporated
  11. additionthe residue was treated with methanol (1 mL) and hydrogen chloride in ether
  12. customSolvents were evaporated
  13. additionthe residue was treated with ether
  14. filtrationThe precipitate was filtered
  15. washwashed with ether

出典と根拠

ORDレコード
ord-6ea39af6375c43879e66d68097d252d9
出典データセット
uspto-grants-2012_02
特許番号
US08124766B2

関連ノート

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