Triethylamine → 5-Pyridin-3-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide

HRID 651638

반응식

HRID 651638 반응식
C(N(CC)CC)C.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[S:18][C:17]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][CH:15]=2)[CH:9]=1.Cl.[NH2:24][C@H:25]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:40]=[C:39]3[C:34]([CH:35]=[CH:36][N:37]=[C:38]3[Cl:41])=[CH:33][CH:32]=2)[C:26]1=[O:42]>CC#N>[Cl:41][C:38]1[C:39]2[C:34](=[CH:33][CH:32]=[C:31]([CH2:30][N:27]3[CH2:28][CH2:29][C@H:25]([NH:24][S:19]([C:17]4[S:18][C:14]([C:10]5[CH:9]=[N:8][CH:13]=[CH:12][CH:11]=5)=[CH:15][CH:16]=4)(=[O:21])=[O:20])[C:26]3=[O:42])[CH:40]=2)[CH:35]=[CH:36][N:37]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 106589765-Pyridin-3-yl-thiophene-2-sulfonyl chlorideHCID 206807083-(S)-Amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride

생성물 1

HCID 206807355-Pyridin-3-yl-thiophene-2-sulfonic acid-[1-(1-chloro-isoquinolin-7-ylmethyl)-2-oxopyrrolidin-3-(S)-yl]-amide수율 63.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Triethylamine (0.35 mL, 2.5 mmol) is added dropwise to a solution of 5-pyridin-3-yl-thiophene-2-sulfonyl chloride (0.22 g, 0.85 mmol) and 3-(S)-amino-1-(1-chloro-isoquinolin-7-ylmethyl)-pyrrolidin-2-one hydrochloride (0.22 g, 0.71 mmol) in CH3CN (5 mL). The suspension is stirred at room temperature overnight then concentrated to dryness. The residue is diluted with methylene chloride and washed with saturated NaHCO3 solution and brine. The organic layer is dried over MgSO4, filtered, concentrated, and then purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2 to give the product (0.23 g, 0.45 mmol) as a white solid.

후처리

  1. concentrationthen concentrated to dryness
  2. additionThe residue is diluted with methylene chloride
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography
  8. washeluting with a gradient of 1% MeOH/CH2Cl2 to 5% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-cc7df4c7111441acb5f91233ac9d297f
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281227B1

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