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

HRID 1800766ノート

反応式

HRID 1800766 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ba89a66fcb64f96a3aca3e52a8dc4b2
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

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