Benzylamine → N-benzyl-2-(4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno[2,3-b]pyridin-4-yl}phenoxy)acetamide

HRID 1830847ノート

反応式

HRID 1830847 の反応式
[Cl:1][C:2]1[C:3]([C:24]2[CH:34]=[CH:33][C:27]([O:28][CH2:29][C:30]([OH:32])=O)=[CH:26][CH:25]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][S:21](=[O:23])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=C1>O.CN(C=O)C>[CH2:35]([NH:42][C:30](=[O:32])[CH2:29][O:28][C:27]1[CH:33]=[CH:34][C:24]([C:3]2[C:2]([Cl:1])=[C:7]([CH2:8][N:9]3[C:10](=[O:15])[CH2:11][CH2:12][C:13]3=[O:14])[N:6]=[C:5]3[S:16][C:17]4[CH2:22][S:21](=[O:23])[CH2:20][CH2:19][C:18]=4[C:4]=23)=[CH:25][CH:26]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 7504BenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22048177(4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno[2,3-b]pyridin-4-yl}phenoxy)acetic acidHCID 220482291-hydroxy-1H-benzimidazole monohydrate

生成物 1

HCID 22048205N-benzyl-2-(4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4',3':4,5]thieno[2,3-b]pyridin-4-yl}phenoxy)acetamide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the compound obtained in Example 115 (104 mg), benzylamine (24 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC, 42 mg), 1-hydroxy-1H-benzimidazole monohydrate (HOBt, 34 mg) and DMF (3 ml) was stirred at room temperature for 10 hours. The reaction mixture was poured into water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4) and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography to obtain N-benzyl-2-(4-{3-chloro-2-[(2,5-dioxo-1-pyrrolidinyl)methyl]-7-oxido-5,8-dihydro-6H-thiopyrano[4′,3′:4,5]thieno[2,3-b]pyridin-4-yl}phenoxy)acetamide from the fraction eluted with ethyl acetate-methanol (6:1) (70 mg, 57%). It was recrystallized from THF-hexane. Colorless prisms. Melting point 220–221° C.

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-d406fa51bdf947b382a4e00998da73d4
出典データセット
uspto-grants-2006_06
特許番号
US07067527B2

反応ノート

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