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 1830847노트

반응식

HRID 1830847 반응식
[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

참가 물질

7

반응물 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

생성물 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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d406fa51bdf947b382a4e00998da73d4
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067527B2

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