Acetyl chloride → Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-chloro-2-fluorophenyl)carbamate

HRID 1800765노트

반응식

HRID 1800765 반응식
[NH2:1][C:2]1[S:3][C:4]2[N:5]=[C:6]([NH:11][C:12]3[C:13]([Cl:27])=[CH:14][C:15]([F:26])=[C:16]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]=3)[N:7]=[CH:8][C:9]=2[N:10]=1.[C:28](Cl)(=[O:30])[CH3:29].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:21]([O:20][C:19](=[O:25])[NH:18][C:16]1[CH:17]=[C:12]([NH:11][C:6]2[N:7]=[CH:8][C:9]3[N:10]=[C:2]([NH:1][C:28](=[O:30])[CH3:29])[S:3][C:4]=3[N:5]=2)[C:13]([Cl:27])=[CH:14][C:15]=1[F:26])([CH3:24])([CH3:22])[CH3:23]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86646100Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-chloro-2-fluorophenyl}carbamate

생성물 1

HCID 91556367Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-chloro-2-fluorophenyl)carbamate

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-chloro-2-fluorophenyl}carbamate (470 mg, 1.14 mmol) in pyridine (10 mL) was added acetyl chloride (204 μL, 2.86 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-chloro-2-fluorophenyl)carbamate as a brown amorphous solid. The obtained compound was used for the next reaction without further purification.

후처리

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 20 mL)
  2. washThe combined organic layer was washed with saturated brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2ba53b94dcf146e7aa80231e5b3432a2
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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