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Sodium Hydroxide → 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid

HRID 655740
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HRID 655740 반응식
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([O:37]CC)=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([OH:37])=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10]
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참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 59402461ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate

생성물 1

HCID 594025252-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid수율 31.8%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To the solution of ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate (Example 67, 120 mg, 0.188 mmol) in methanol (20 mL) was added 2N sodium hydroxide (3 mL) in a dropwise fashion at 0° C. The reaction mixture was stirred overnight and then concentrated under reduced pressure to dryness. The resulting residue was diluted with water (20 mL) and extracted with ethyl acetate to remove any organic impurities. The aqueous layer was passed through celite bed and acidified with 2N hydrochloric acid. The precipitated product was collected by filtration and dried to afford 35 mg (31.8%) of 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid as a yellow solid.

후처리

  1. concentrationconcentrated under reduced pressure to dryness
  2. additionThe resulting residue was diluted with water (20 mL)
  3. extractionextracted with ethyl acetate
  4. customto remove any organic impurities
  5. filtrationThe precipitated product was collected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-fae2bf4e7a584e38937584258980d524
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071605B2

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