2-(Methylamino)ethanol → HCID 67486870, compound

HRID 1994970Notes

Reaction equation

HRID 1994970 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([N:15]([CH3:25])[S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)(=[O:18])=[O:17])[CH:14]=1)[NH:11][C:10]([C:26]1[S:27][CH:28]([CH2:31][C:32](O)=[O:33])[CH2:29][N:30]=1)=[CH:9]2.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:57][NH:58][CH2:59][CH2:60][OH:61]>O.CN(C)C=O>[OH:61][CH2:60][CH2:59][N:58]([CH3:57])[C:32](=[O:33])[CH2:31][CH:28]1[S:27][C:26]([C:10]2[NH:11][C:12]3[C:8]([CH:9]=2)=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:14][C:13]=3[N:15]([CH3:25])[S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)(=[O:17])=[O:18])=[N:30][CH2:29]1

Participants

7

Reactant 4

HCID 80162-(Methylamino)ethanolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68461826HCID 68461826, compound

Product 1

HCID 67486870HCID 67486870, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-{5-(2-methoxyethoxy)-7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (250 mg), 1H-1,2,3-benzotriazol-1-ol (100 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (140 mg), 2-(methylamino)ethanol (60 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 15 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-methanol (100:0-95:5, volume ratio) to give colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (140 mg, yield 50%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-methanol (100:0-95:5, volume ratio)
  6. customto give colorless crystals
  7. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0ce711c931ce411793f4d97f4d38e0af
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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