Dichloromethane → HCID 68928942, compound

HRID 1845715Notes

Reaction equation

HRID 1845715 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]([CH3:30])([CH3:29])[CH2:10][N:11]1[C:23]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:24])[C:14]=2[N:13]=[C:12]1[CH2:25][O:26][CH2:27][CH3:28].ClCCl>CN(C=O)C>[O:5]=[C:4]1[CH2:3][CH2:2][C:1](=[O:6])[N:24]1[C:15]1[C:14]2[N:13]=[C:12]([CH2:25][O:26][CH2:27][CH3:28])[N:11]([CH2:10][C:9]([NH:8][C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])([CH3:29])[CH3:30])[C:23]=2[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7922Succinic anhydrideHCID 10380870TLR7/8 agonist 3

Product 1

HCID 68928942HCID 68928942, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Succinic anhydride (3.20 g, 32.0 mmol) was added to a 100° C. solution of 1-(2-amino-2-methylpropyl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in U.S. Patent Publication No. 2004/0091491, 2.00 g, 6.39 mmol) in DMF (20 mL). After 2 days, the reaction mixture was concentrated under reduced pressure to give an off-white solid. The solid was stirred with 100 mL of dichloromethane and was isolated by filtration. The filtrate was concentrated, stirred with dichloromethane (25 mL), and filtered to yield additional solid. The combined solids were dried under vacuum to give 3.16 g of 4-({2-[4-(2,5-dioxopyrrolidin-1-yl)-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}amino)-4-oxobutanoic acid as a white solid that was used without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto give an off-white solid
  3. customwas isolated by filtration
  4. concentrationThe filtrate was concentrated
  5. filtrationfiltered
  6. customto yield additional solid
  7. customThe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-0fb8c419769f46db8074a33157090559
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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