Triethylamine → Hexanamide

HRID 1845714

반응식

HRID 1845714 반응식
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]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 100682N-Succinimidyl 3-(2-pyridyldithio)propionateHCID 68926228HCID 68926228, 화합물2회

생성물 2

HCID 12332HexanamideHCID 11854967HCID 11854967, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5eb401bdb94433cbe81cf7ec868da39
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951528B2

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