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Hydrochloric Acid → (S)-N-(3-(5-(2-(2-aminopropylamino)pyrimidin-4-yl)-2-cyclopropyl-1H-imidazol-4-yl)-2-chlorophenyl)propane-1-sulfonamide

HRID 535771
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HRID 535771 반응식
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:15]1[N:16]=[C:17]([CH:46]2[CH2:48][CH2:47]2)[N:18](COCC[Si](C)(C)C)[C:19]=1[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][C@@H:28]([NH:30]C(=O)OC(C)(C)C)[CH3:29])[N:21]=1.Cl>CCO>[NH2:30][C@@H:28]([CH3:29])[CH2:27][NH:26][C:22]1[N:21]=[C:20]([C:19]2[NH:18][C:17]([CH:46]3[CH2:48][CH2:47]3)=[N:16][C:15]=2[C:3]2[C:2]([Cl:1])=[C:7]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=2)[CH:25]=[CH:24][N:23]=1
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참가 물질

4

반응물 2

HCID 313Hydrochloric Acid2회HCID 69811403(S)-tert-butyl 1-(4-(4-(2-chloro-3-(propylsulfonamido)phenyl)-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate

생성물 1

HCID 69809521(S)-N-(3-(5-(2-(2-aminopropylamino)pyrimidin-4-yl)-2-cyclopropyl-1H-imidazol-4-yl)-2-chlorophenyl)propane-1-sulfonamide수율 107.1%

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
60 °C

실험 절차

A solution of (S)-tert-butyl 1-(4-(4-(2-chloro-3-(propylsulfonamido)phenyl)-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate (116 mg, 0.14 mmol) in EtOH (2 mL) was treated with aqueous 6.0 N HCl solution (0.8 mL, 4.8 mmol) and the resulting reaction was heated to 60° C. for 30 minutes, then at room temperature for 40 minutes. The reaction was allowed to cool to room temperature and the volatiles were removed in vacuo. Further drying under high vacuum afforded (S)—N-(3-(5-(2-(2-aminopropylamino)pyrimidin-4-yl)-2-cyclopropyl-1H-imidazol-4-yl)-2-chlorophenyl)propane-1-sulfonamide (80 mg, 0.15 mmol) as the HCl salt (4A-2) which was used without further purification: LCMS (m/z) 490.2 (MH+), tR=0.48 minute.

후처리

  1. customthe resulting reaction
  2. temperatureto cool to room temperature
  3. customthe volatiles were removed in vacuo
  4. customFurther drying under high vacuum

출처 및 근거

ORD 기록
ord-8a5903f980724b85bcba61c2f58e2f03
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859548B2

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