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Hydrochloric Acid → 4-({4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoic acid

HRID 1946817
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HRID 1946817 반응식
[CH:1]1([N:7]([CH2:34][CH:35]2[CH2:37][CH2:36]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][CH2:28][C:29]([O:31]CC)=[O:30])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1>[CH:1]1([N:7]([CH2:34][CH:35]2[CH2:36][CH2:37]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59447011Ethyl 4-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoate

생성물 1

HCID 594468314-({4-[({6-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoic acid수율 81.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
0 °C

실험 절차

A solution of ethyl 4-({4-[({6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidin-4-yl}carbonyl)amino]phenyl}sulfonyl)butanoate (Example 131, 80 mg; 0.16 mmol) in THF (5 ml) was treated with 10% sodium hydroxide solution (20 ml). After stirring for 45 minutes the mixture was cooled to 0° C. and acidified with concentrated HCl. The mixture was extracted with EtOAc and the combined organic extracts washed with water, passed through a hydrophobic frit and the solvent removed in vacuo. The residue was purified by column chromatography (silica) eluting with DCM containing increasing amounts of methanol to give the title compound as a white solid (65 mg, 81%).

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washthe combined organic extracts washed with water
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography (silica)
  5. washeluting with DCM containing
  6. temperatureincreasing amounts of methanol

출처 및 근거

ORD 기록
ord-3e12bf84720748abbfd20fbbb208cb41
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399448B2

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