Anisole → N-{5-[(5-amino-2-chloro-4-fluorophenyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide

HRID 1800766노트

반응식

HRID 1800766 반응식
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[N:23]=[C:22]([NH:24][C:25](=[O:27])[CH3:26])[S:21][C:19]=3[N:20]=2)[C:11]([Cl:28])=[CH:10][C:9]=1[F:29])(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:29])=[CH:10][C:11]([Cl:28])=[C:12]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[N:23]=[C:22]([NH:24][C:25](=[O:27])[CH3:26])[S:21][C:19]=3[N:20]=2)[CH:13]=1

참가 물질

4

반응물 2

HCID 7519AnisoleHCID 91556367Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-chloro-2-fluorophenyl)carbamate

생성물 1

HCID 86646101N-{5-[(5-amino-2-chloro-4-fluorophenyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide수율 74%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of the above-mentioned crude product of tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl]amino}-4-chloro-2-fluorophenyl)carbamate and anisole (1 mL) in trifluoroacetic acid (15 mL) was stirred at 0° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (30 mL) was added to the obtained residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 10 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. The obtained residue was washed with ethyl acetate to give the title compound (297 mg, 74%) as a yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (30 mL)
  2. additionwas added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 mL, 10 mL)
  4. washThe combined organic layer was washed with saturated brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate

출처 및 근거

ORD 기록
ord-1ba89a66fcb64f96a3aca3e52a8dc4b2
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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