Ammonia → (S)-4-Amino-N-(1-cyano-2-(4-(1-oxoisoindolin-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216940ノート

反応式

HRID 216940 の反応式
[C:1]([C@@H:3]([NH:21][C:22]([C:24]1([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][CH2:14]3)=[CH:7][CH:6]=1)#[N:2].N>C(O)=O.O>[NH2:30][C:24]1([C:22]([NH:21][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[C:16](=[O:20])[NH:15][CH2:14]4)=[CH:9][CH:10]=2)=[O:23])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

参加物

5

反応物 2

HCID 222AmmoniaHCID 59568570(S)-tert-Butyl 4-(1-cyano-2-(4-(1-oxoisoindolin-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 46944250(S)-4-Amino-N-(1-cyano-2-(4-(1-oxoisoindolin-5-yl)phenyl)ethyl)tetrahydro-2H-pyran-4-carboxamide収率 54.6%

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 962Water溶媒

実験手順

(S)-tert-Butyl 4-(1-cyano-2-(4-(1-oxoisoindolin-5-yl)phenyl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 15, step (ii), 160 mg) was stirred in formic acid (0.5 mL) at 50° C. for 20 min. The reaction mixture was cooled to room temperature and the mixture diluted with water (20 mL). The solution was basified with 0.880 ammonia and extracted into ethyl acetate (100 mL). The extract was dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica using methanol/ethyl acetate (1/9) to afford the titled compound as a solid (70 mg).

後処理

  1. extractionextracted into ethyl acetate (100 mL)
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography on silica

出典と根拠

ORDレコード
ord-cf8de84d06b04181b7b8564b4982ecba
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

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