1-Hydroxybenzotriazole → HCID 59303536, compound

HRID 504766Notes

Reaction equation

HRID 504766 reaction equation
[CH3:1][N:2]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)(=[O:25])=[O:24])[C:3]1[CH:4]=[C:5]([O:15][CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12](O)=[O:13])=[CH:8]2.[CH2:32]([S:39][CH:40]([CH:43]([O:46][CH3:47])[O:44][CH3:45])[CH2:41][NH2:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>O.CN(C)C=O>[CH2:32]([S:39][CH:40]([CH:43]([O:44][CH3:45])[O:46][CH3:47])[CH2:41][NH:42][C:12]([C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[CH:6][C:5]([O:15][CH2:16][CH2:17][CH2:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:4][C:3]=2[N:2]([CH3:1])[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)(=[O:24])=[O:25])=[O:13])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 574759902-(Benzylthio)-3,3-dimethoxypropan-1-amineHCID 57476201HCID 57476201, compound

Product 1

HCID 59303536HCID 59303536, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-[methyl(pyridin-2-ylsulfonyl)amino]-5-[3-(methylsulfonyl)propoxy]-1H-indole-2-carboxylic acid (2.10 g), 2-(benzylthio)-3,3-dimethoxypropan-1-amine (1.30 g), 1H-1,2,3-benzotriazol-1-ol (730 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (1.04 g) and N,N-dimethylformamide (50 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 obtained residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (1:4-1:9, volume ratio) to give the title compound (2.70 g, yield 87%) as a colorless amorphous solid.

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 hexane-ethyl acetate (1:4-1:9, volume ratio)

Sources & evidence

ORD record
ord-3b29ec8f26854199bc17ac0101b373a1
Source dataset
uspto-grants-2010_08
Patent number
US07777047B2

Reaction notes

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