Trifluoroacetic anhydride → N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1851548ノート

反応式

HRID 1851548 の反応式
[CH3:1][N:2]([S:22]([C:25]1[S:26][CH:27]=[CH:28][CH:29]=1)(=[O:24])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19]([NH2:21])=O)=[CH:15][N:16]=1)=[CH:8]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([CH2:18][CH2:17][C:14]1[S:13][C:12]([C:9]2[NH:10][C:11]3[C:7]([CH:8]=2)=[CH:6][CH:5]=[CH:4][C:3]=3[N:2]([CH3:1])[S:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)(=[O:24])=[O:23])=[N:16][CH:15]=1)#[N:21]

参加物

4

反応物 2

HCID 9845Trifluoroacetic anhydrideHCID 57901592HCID 57901592、化合物

生成物 1

HCID 57901663N-{2-[5-(2-Cyanoethyl)-1,3-thiazol-2-yl]-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide収率 95%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mixture of 3-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazol-5-yl)propanamide (1.32 g) and pyridine (15 mL) was added trifluoroacetic anhydride (0.90 mL) at 0° C. over 15 min. The reaction mixture was stirred at room temperature for 2 hr and concentrated. 10% Aqueous citric acid solution was added to the residue. The resulting crystals were collected by filtration, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography and the title compound (1.20 g, yield 95%) was obtained as yellow crystals from a fraction eluted with tetrahydrofuran-hexane (2:1, volume ratio). melting point 207-208° C.

後処理

  1. concentrationconcentrated
  2. addition10% Aqueous citric acid solution was added to the residue
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried

出典と根拠

ORDレコード
ord-11ca78c5e3fc4d7a807cc92f6955fd30
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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