Trifluoroacetic anhydride → HCID 57901755、化合物

HRID 1851346ノート

反応式

HRID 1851346 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([NH2:21])=O)=[CH:15]2)(=[O:8])=[O:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8])#[N:21]

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 57476167HCID 57476167、化合物

生成物 1

HCID 57901755HCID 57901755、化合物収率 92%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (4.65 g) and pyridine (20 mL) was slowly added trifluoroacetic anhydride (4.50 mL) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography, and eluted with tetrahydrofuran-hexane (2:3, volume ratio). The eluate was treated with activated carbon and concentrated to give the title compound (4.04 g, yield 92%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point 283-284° C.

後処理

  1. customat 0° C.
  2. concentrationThe reaction mixture was concentrated
  3. addition10% aqueous citric acid solution was added
  4. filtrationthe resulting crystals were filtrated
  5. washwashed with water
  6. customdried
  7. washeluted with tetrahydrofuran-hexane (2:3, volume ratio)
  8. additionThe eluate was treated with activated carbon
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-cda5f657b65a4009acf0d2644afd8497
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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