Diisopropylethylamine → 4-((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexylamino)-2-(3-(5-methyl-1H-tetrazol-1-yl)phenethylamino)pyrimidine-5-carbonitrile

HRID 1749487ノート

反応式

HRID 1749487 の反応式
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2CCN)[N:5]=[N:4][N:3]=1.[OH:16][C@H:17]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]2[C:29]([C:30]#[N:31])=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=2)[CH2:19][C:18]1([CH3:37])[CH3:36].O[C@H]1CC[C@@H:42]([NH:45]C2C(C#N)=CN=C(S(C)=O)N=2)[CH2:41]C1(C)C.CCN(C(C)C)C(C)C>>[OH:16][C@H:17]1[CH2:22][CH2:21][C@@H:20]([NH:23][C:24]2[C:29]([C:30]#[N:31])=[CH:28][N:27]=[C:26]([NH:45][CH2:42][CH2:41][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([N:6]4[C:2]([CH3:1])=[N:3][N:4]=[N:5]4)[CH:12]=3)[N:25]=2)[CH2:19][C:18]1([CH3:37])[CH3:36]

参加物

5

反応物 4

HCID 81531DiisopropylethylamineHCID 825065682-(2-(5-methyl-1H-tetrazol-1-yl)phenyl)ethanamineHCID 1181621034-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrileHCID 1181621344-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile

生成物 1

HCID 1181622534-((1R,4S)-4-Hydroxy-3,3-dimethylcyclohexylamino)-2-(3-(5-methyl-1H-tetrazol-1-yl)phenethylamino)pyrimidine-5-carbonitrile収率 21%

反応条件

温度
100 °C

実験手順

A mixture of 2-(2-(5-methyl-1H-tetrazol-1-yl)phenyl)ethanamine (85 mg, 0.42 mmol), 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile and 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile (90 mg, 0.27 mmol) and DIEA (105 mg, 0.81 mmol) was stirred at 100° C. under microwave irradiation for 1.5 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by standard methods to give the title compound (44.3 mg, 0.073 mmol, 21% yield). 1H NMR (400 MHz, CD3OD) δ (ppm) 7.92 (m, 1H), 7.50-7.40 (m, 2H), 7.34-7.25 (m, 2H), 4.25-4.15 (m, 1H), 3.68-3.49 (m, 2H), 3.25-3.22 (m, 1H), 3.00-2.87 (m, 2H), 2.46 (s, 3H), 1.79-1.22 (m, 6H), 0.88-0.83 (m, 6H). MS (ESI) m/z 448.2 [M+H]+.

後処理

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by standard methods

出典と根拠

ORDレコード
ord-51dfac5189ad41f8b97ac05190b80155
出典データセット
uspto-grants-2015_10
特許番号
US09156798B2

反応ノート

読み込み中…