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1-Hydroxybenzotriazole → 4-Oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamide

HRID 1851550
Notes
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Reaction equation

HRID 1851550 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[O:16]=[C:17]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:18][CH2:19][C:20](O)=[O:21].N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O>[O:16]=[C:17]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[CH2:18][CH2:19][C:20]([NH:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)=[CH:14]2)=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 783853-(2-Thenoyl)propionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579018012-(1,3-Thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 579017094-Oxo-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-4-(2-thienyl)butanamideYield 220.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-(1,3-thiazol-2-yl)-1H-indole-7-amine (0.31 g), 4-oxo-4-(2-thienyl)butanoic acid (0.89 g), 1H-1,2,3-benzotriazol-1-ol (0.75 g) and N,N-dimethylformamide (20 mL) was added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.06 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (1.21 g, yield. 69%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio). melting point 140-141° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-28e8b3d10d7b4d95b2f83fcae06506e0
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08957070B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes