Morpholine → HCID 57657247, compound

HRID 244833Notes

Reaction equation

HRID 244833 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:22][CH2:23][C:24]([OH:26])=O)=[CH:5][C:4]=2[N:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH3:21])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:22][CH2:23][C:24]([N:48]3[CH2:53][CH2:52][O:51][CH2:50][CH2:49]3)=[O:26])=[CH:5][C:4]=2[N:3]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69079561HCID 69079561, compound

Product 1

HCID 57657247HCID 57657247, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-[4-Amino-2-ethyl-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoic acid (500 mg, 1.4 mmol), chloroform (100 mL) and 1-hydroxybenzotriazole (575 mg, 4.26 mmol) were combined and then stirred for 30 minutes. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (1.00 g, 5.2 mmol) was added and the reaction was stirred for 30 minutes. Morpholine (10 mL) was added in one portion. After 4 hours, 1% aqueous sodium carbonate (100 mL) was added and the mixture was stirred. The fractions were separated and the organic fraction was sequentially washed with 1% aqueous sodium carbonate (50 mL), dried (MgSO4), filtered, and concentrated to a white solid. Recrystallization from acetonitrile provided 225 mg of 3-[4-amino-2-ethyl-1-(2-hydroxy-2-methyl-propyl)-1H-imidazo[4,5-c]quinolin-7-yl]-1-(morpholin-4-yl)propan-1-one as a white solid, mp 237-239° C.

Workup

  1. stirringthe reaction was stirred for 30 minutes
  2. waitAfter 4 hours
  3. stirringthe mixture was stirred
  4. customThe fractions were separated
  5. washthe organic fraction was sequentially washed with 1% aqueous sodium carbonate (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid
  9. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-4e9e73e623e84439bcf7c1dddf32f185
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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