Triethylamine → [2-Amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone

HRID 30110

반응식

HRID 30110 반응식
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:6][CH:5]=[C:4]([NH:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[N:3]=1.C(N(CC)CC)C.[CH2:31]([S:33](Cl)(=[O:35])=[O:34])[CH3:32]>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:6][CH:5]=[C:4]([NH:17][CH:18]2[CH2:19][CH2:20][N:21]([S:33]([CH2:31][CH3:32])(=[O:35])=[O:34])[CH2:22][CH2:23]2)[N:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 58590835[2-Amino-6-(piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone

생성물 1

HCID 11538717[2-Amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone수율 60.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a solution of [2-Amino-6-(piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone (19.2 mg, 0.0611 mmol, Example 9) in methylene chloride (1.5 mL) were added triethylamine (12.6 mg, 0.124 mmol, Aldrich) in methylene chloride (0.2 mL) and a solution of ethanesulfonyl chloride (8.66 mg, 0.066 mmol, Aldrich 99+%) in methylene chloride (0.2 mL) at room temperature. After ˜30 mins the reaction mixture was concentrated and purified by reversed phase HPLC as described in Example 11 to give [2-Amino-6-(1-ethanesulfonyl-piperidin-4-ylamino)-pyridin-3-yl]-(2-fluoro-phenyl)-methanone as a white solid (15.1 mg, 60 % yield). HRMS, observed: 407.1533, calcd for (M+H)+: 407.1548.

후처리

  1. customat room temperature
  2. concentrationAfter ˜30 mins the reaction mixture was concentrated
  3. custompurified by reversed phase HPLC

출처 및 근거

ORD 기록
ord-8117802aa89c4f1cbc3d4798825a5288
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423051B2

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