Triethylamine → Hexanamide

HRID 1845714

反応式

HRID 1845714 の反応式
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]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 100682N-Succinimidyl 3-(2-pyridyldithio)propionateHCID 68926228HCID 68926228、化合物2 回

生成物 2

HCID 12332HexanamideHCID 11854967HCID 11854967、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5eb401bdb94433cbe81cf7ec868da39
出典データセット
uspto-grants-2015_02
特許番号
US08951528B2

関連ノート

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