Water → 2-[[(1R,2S)-2-aminocyclohexyl]amino]-4-(3-fluoro-4-pyrazol-1-ylanilino)pyrimidine-5-carboxamide

HRID 558997ノート

反応式

HRID 558997 の反応式
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=O)OC(C)(C)C.N1(OC2[N:31]=[C:30]([NH:32][C:33]3[CH:38]=[CH:37][C:36]([N:39]4[CH:43]=[CH:42][CH:41]=[N:40]4)=[C:35]([F:44])[CH:34]=3)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=2)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[N:31]=[C:30]([NH:32][C:33]2[CH:38]=[CH:37][C:36]([N:39]3[CH:43]=[CH:42][CH:41]=[N:40]3)=[C:35]([F:44])[CH:34]=2)[C:29]([C:45]([NH2:47])=[O:46])=[CH:28][N:27]=1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 574718772-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamide

生成物 1

HCID 445186572-[[(1R,2S)-2-aminocyclohexyl]amino]-4-(3-fluoro-4-pyrazol-1-ylanilino)pyrimidine-5-carboxamide収率 58.8%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of tert-butyl (1S,2R)-2-aminocyclohexylcarbamate (0.30 M in NMP, 2.00 mL, 0.600 mmol) in NMP (2 mL) was added to 2-(1H-benzo[d][1,2,3]triazol-1-yloxy)-4-(3-fluoro-4-(1H-pyrazol-1-yl)phenylamino)pyrimidine-5-carboxamide (184 mg, 0.427 mmol). DIEA (0.150 mL, 0.863 mmol) was also added. The mixture was stirred at 90 C overnight. After being cooled to room temperature, water was added to induce precipitation. The precipitate was collected, then dissolved in CH2Cl2 (5 mL) and TFA (4 mL). The solution was stirred at room temperature for 30 min. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (103 mg). MS 411.5 (M+H). UV λ=238.8, 304.8 nm.

後処理

  1. customprecipitation
  2. customThe precipitate was collected
  3. dissolutiondissolved in CH2Cl2 (5 mL)
  4. stirringThe solution was stirred at room temperature for 30 min
  5. concentrationIt was concentrated in vacuo
  6. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-777a4ab6a87748b38d1bc7564c4589a4
出典データセット
uspto-grants-2011_11
特許番号
US08063058B2

反応ノート

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