Triethylamine → Hexanamide

HRID 1845714Notes

Reaction equation

HRID 1845714 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([NH:10][C:11]([CH3:32])([CH3:31])[CH2:12][N:13]1[C:25]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:26])[C:16]=2[N:15]=[C:14]1[CH2:27][O:28][CH2:29][CH3:30])=[O:9].C(N(CC)CC)C.C1C(=O)N([O:47][C:48]([CH2:50][CH2:51][S:52][S:53][C:54]2[N:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=O)C(=O)C1>O1CCCC1.CN(C=O)C>[NH2:26][C:17]1[C:16]2[N:15]=[C:14]([CH2:27][O:28][CH2:29][CH3:30])[N:13]([CH2:12][C:11]([NH:10][C:8](=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2][C:48](=[O:47])[CH2:50][CH2:51][S:52][S:53][C:54]3[CH:55]=[CH:56][CH:57]=[CH:58][N:59]=3)([CH3:31])[CH3:32])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1.[C:8]([NH2:10])(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 100682N-Succinimidyl 3-(2-pyridyldithio)propionateHCID 689262286-Amino-n-{2-[4-amino-2-(ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}hexanamide hydrochloride2×

Product 2

HCID 12332HexanamideHCID 11854967N-{2-{4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-6-{[3-(pyridin-2-yldithio)propanoyl]amino}hexanamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-6-{[3-(pyridin-2-yldithio)propanoyl]amino}hexanamide was synthesized from 6-amino-N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}hexanamide hydrochloride in one step. A mixture of 6-amino-N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}hexanamide hydrochloride (68 mg, 0.16 mmol), triethylamine (0.046 mL, 0.32 mmol), and N-succinimidyl 3-(2-pyridyldithio)propionate in tetrahydrofuran (1.6 mL) and DMF (0.5 mL) was stirred at room temperature for 5 hours. The reaction mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel to provide 36 mg of N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-6-{[3-pyridin-2-yldithio)propanoyl]amino}hexanamide as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f5eb401bdb94433cbe81cf7ec868da39
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

Loading…