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Triethylamine → 1-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride

HRID 1645351
ノート
印刷プレビュー

反応式

HRID 1645351 の反応式
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:9][CH:10]=2)[CH:5]=[C:4]1[C:17]([OH:19])=O)[CH3:2].C(Cl)(=O)C([Cl:23])=O.[CH3:26][O:27][CH2:28][CH2:29][N:30]([CH3:38])[C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][N:32]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[ClH:23].[CH3:26][O:27][CH2:28][CH2:29][N:30]([CH3:38])[C:31]1[N:32]=[CH:33][C:34]([NH:37][C:17]([C:4]2[N:3]([CH2:1][CH3:2])[C:11]3[C:6]([CH:5]=2)=[CH:7][C:8]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:9][CH:10]=3)=[O:19])=[CH:35][CH:36]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 52937159N2-(2-methoxyethyl)-N2-methylpyridine-2,5-diamineHCID 593651711-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid

生成物 1

HCID 667724081-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 1-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid (65 mg, 0.24 mmol), CH2Cl2 (5 mL), and catalytic amount of DMF was stirred under Ar, and oxalyl chloride (2M in dichloromethane, 250 μL, 0.5 mmol) was dripped into the mixture over 5 min. The mixture was stirred at room temperature for 1.0 hr and then concentrated to dryness. Benzene was added and the solution was evaporated to dryness again. The residue was re-dissolved in 5 mL of CH2Cl2 and dripped, under Ar, into a solution of N-(2-methoxy-ethyl)-N-methyl-pyridine-2,5-diamine (43.0 mg, 0.24 mmol), and triethylamine (0.52 mg, 0.5 mmol) in 5 mL of CH2Cl2. The reaction was stirred at room temperature for 0.5 hr then concentrated and the residue was taken up in 50 mL of EtOAc and washed with 50 mL of saturated ammonium chloride, brine and dried with anhydrous sodium sulfate. The solvent was removed, and the crude product was purified by flash chromatography (hexanes:EtOAc) followed by conversion to HCl salt with 1N HCl in ether to afford the product, 1-ethyl-5-trifluoromethoxy-1H-indole-2-carboxylic acid {6-[(2-methoxy-ethyl)-methyl-amino]-pyridin-3-yl}-amide hydrochloride, as a pink solid (44 mg, 42% yield). LCMS for C21H23F3N4O3 calcd. (m/e) 436, observed 437 (M+H).

後処理

  1. concentrationconcentrated to dryness
  2. additionBenzene was added
  3. customthe solution was evaporated to dryness again
  4. dissolutionThe residue was re-dissolved in 5 mL of CH2Cl2
  5. stirringThe reaction was stirred at room temperature for 0.5 hr
  6. concentrationthen concentrated
  7. washwashed with 50 mL of saturated ammonium chloride, brine
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was removed
  10. customthe crude product was purified by flash chromatography (hexanes:EtOAc)

出典と根拠

ORDレコード
ord-3a162519961c43b8b5c694683a9aedf7
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08124766B2

反応ノート

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