2-Thiopheneacetyl chloride → (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester

HRID 382068ノート

反応式

HRID 382068 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:21]/[C:22]2[NH:23][CH:24]=[CH:25][C:26]=2[O:27][CH3:28])/[C:13](=[O:20])[NH:14]3)=[CH:6][CH:5]=1.[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](Cl)=[O:37]>C([O-])(O)=O.[Na+].C1COCC1>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:18]([NH:19][C:36](=[O:37])[CH2:35][C:31]3[S:30][CH:34]=[CH:33][CH:32]=3)=[CH:17][CH:16]=[C:15]3[C:11]=2/[C:12](=[CH:21]/[C:22]2[NH:23][CH:24]=[CH:25][C:26]=2[O:27][CH3:28])/[C:13](=[O:20])[NH:14]3)=[CH:6][CH:5]=1

参加物

5

反応物 2

HCID 1623622-Thiopheneacetyl chlorideHCID 9821703(Z)-4-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester

生成物 1

HCID 9871087(Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester収率 90.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Using Method M above, (Z)-4-[5-amino-2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-oxo-1H-indol-4-yl]-benzoic acid methyl ester (310 mg, 0.8 mmol) (from Example 46 supra) was acylated with 2-thiopheneacetyl chloride (260 mg, 1.6 mmol) (Aldrich) in saturated aqueous NaHCO3 (1.6 mL) and THF (15 mL) at room temperature for 3 h to yield (Z)-4-[2,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl) methylene]-2-oxo-5-[(2-thienylacetyl)amino]-1H-indol-4-yl]-benzoic acid methyl ester (yield 370 mg, 90%).

出典と根拠

ORDレコード
ord-22fbae50353744f9b396fe2a91a5de53
出典データセット
uspto-grants-2001_10
特許番号
US06307056B1

反応ノート

読み込み中…