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 1830847Notes

Reaction equation

HRID 1830847 reaction equation
[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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d406fa51bdf947b382a4e00998da73d4
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

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