Hydrochloric Acid → 4-(8-[1,4]Diazepan-1-yl-6-methyl-quinolin-7-yloxy)-butyric acid methyl ester

HRID 2063575Notes

Reaction equation

HRID 2063575 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:16]([O:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:17]([CH3:25])[CH:18]=[C:19]3[C:24]=2[N:23]=[CH:22][CH:21]=[CH:20]3)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[CH3:33][O:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][O:26][C:16]1[C:15]([N:11]2[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]2)=[C:24]2[C:19]([CH:20]=[CH:21][CH:22]=[N:23]2)=[CH:18][C:17]=1[CH3:25]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 593661754-[7-(3-Methoxycarbonyl-propoxy)-6-methyl-quinolin-8-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 593662074-(8-[1,4]Diazepan-1-yl-6-methyl-quinolin-7-yloxy)-butyric acid methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The product from step 1 was dissolved in MeOH (18.8 mL) and HCl was added (4M in dioxane, 18.8 mL, 75.2 mmol). The reaction was stirred at room temperature for 2 h, then concentrated. CH2Cl2 was added and this solution was washed with sat. aq. NaHCO3, then brine. The organic was dried over MgSO4, filtered, and concentrated to give the product (1.30 g, 96% yield) as an oil.

Workup

  1. concentrationconcentrated
  2. additionCH2Cl2 was added
  3. washthis solution was washed with sat. aq. NaHCO3
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3af34e9f423f4ea7b503b30b12d59738
Source dataset
uspto-grants-2012_10
Patent number
US08288373B2

Reaction notes

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