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

HRID 1749487노트

반응식

HRID 1749487 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

반응 조건

온도
100 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-51dfac5189ad41f8b97ac05190b80155
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156798B2

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