Chloroacetyl chloride → 3-amino-6-(2-chloro-acetyl)-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide

HRID 2375367ノート

反応式

HRID 2375367 の反応式
Cl.[NH2:2][C:3]1[C:14]2[C:6](=[N:7][C:8]3[CH2:9][NH:10][CH2:11][C:12]=3[C:13]=2[C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[S:5][C:4]=1[C:20]([NH2:22])=[O:21].C(N(C(C)C)CC)(C)C.[Cl:32][CH2:33][C:34](Cl)=[O:35]>CN(C=O)C.C1COCC1>[NH2:2][C:3]1[C:14]2[C:6](=[N:7][C:8]3[CH2:9][N:10]([C:34](=[O:35])[CH2:33][Cl:32])[CH2:11][C:12]=3[C:13]=2[C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)[S:5][C:4]=1[C:20]([NH2:22])=[O:21]

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 689136683-Amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochloride

生成物 1

HCID 598548793-amino-6-(2-chloro-acetyl)-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To 50 mg (0.158 mmol) of 3-amino-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide hydrochloride in 3.0 ml of DMF was added dropwise 0.32 ml of 1.0 M solution containing diisopropylethylamine (DIPEA) in THF and (0.16 mmol) of 2-chloroacetyl chloride in 1.0 ml of DMF, according to standard procedures. The resulting mixture was continuously stirred at room temperature for several hours, and the progress of the reaction was monitored by TLC. The solvent was removed under vacuum, and the residue was recrystallized from a polar solvent. Similar procedures were used for 3-amino-6-[2-(4-benzyl-cyclohexylamino)-acetyl]-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide (103) and 3-amino-6-(6-morpholin-4-yl-pyridine-3-carbonyl)-4-thiophen-2-yl-6,7-dihydro-5H-1-thia-6,8-diaza-s-indacene-2-carboxylic acid amide (105). In some cases, if the product was not recrystallized from methanol or ethanol, the reaction mixture was purified by flash column chromatography or preparative HPLC. All products were verified by NMR spectroscopy.

後処理

  1. customThe solvent was removed under vacuum
  2. customthe residue was recrystallized from a polar solvent
  3. customIn some cases, if the product was not recrystallized from methanol or ethanol
  4. customthe reaction mixture was purified by flash column chromatography or preparative HPLC

出典と根拠

ORDレコード
ord-0618708822ba476cb6da7445241b1780
出典データセット
uspto-grants-2008_12
特許番号
US07465742B2

反応ノート

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