Hydrochloric Acid → HCID 69457310, compound

HRID 1351960Notes

Reaction equation

HRID 1351960 reaction equation
[OH:1][C@H:2]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C@@H:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[C:12]([C:17]([OH:19])=O)[CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[CH3:4].Cl.[CH2:28]([NH2:30])[CH3:29].C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.Cl.ON1C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>CN(C)C=O.CO>[CH2:28]([NH:30][C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[NH:10][CH:9]=[C:8]2[CH2:7][CH2:6][NH:5][C@@H:3]([CH3:4])[C@H:2]([OH:1])[C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)=[O:19])[CH3:29]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 69458988HCID 69458988, compound

Product 1

HCID 69457310HCID 69457310, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl)ethylamino]ethyl}-1H-indole-7-carboxylic acid (29.1 mg, 0.0821 mmol) in N,N-dimethylformamide (3 mL) are added ethylamine hydrochloride (67 mg, 0.822 mmol), triethylamine (171 μL, 1.23 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (WSCI) hydrochloride (78.7 mg, 0.411 mmol) and 1-hydroxybenzotriazole (HOBt, 55.5 mg, 0.411 mmol), and the mixture is stirred at room temperature for 17 hours. The reaction solution is poured into a saturated aqueous sodium hydrogen carbonate solution, and the mixture is separated into chloroform. The organic layer is washed with a saturated brine and dried over anhydrous sodium sulfate. The solvent is removed by distillation, and the resulting crude product is purified by preparative TLC (a saturated ammonia solution in chloroform:methanol=20:1) to give 3-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-(methyl)ethyl-amino]ethyl}-1H-indole-7-carboxylic acid ethylamide (7.5mg, 0.0197 mmol, 24%).

Workup

  1. customthe mixture is separated into chloroform
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is removed by distillation
  5. customthe resulting crude product is purified by preparative TLC (a saturated ammonia solution in chloroform

Sources & evidence

ORD record
ord-08585f31c4fc419a8f9b37a18dd0161b
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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