Chlorocyclohexane → HCID 67470905、化合物

HRID 928239

反応式

HRID 928239 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([NH:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=2)[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:21]1(Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CN(C=O)C>[CH:21]1([N:4]2[C:5]3=[N:6][C:7]([NH:11][CH2:12][CH2:13][CH3:14])=[N:8][CH:9]=[C:10]3[C:2]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:3]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

8

反応物 4

HCID 10952ChlorocyclohexaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 178456834HCID 178456834、化合物

生成物 1

HCID 67470905HCID 67470905、化合物収率 67.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
200 °C

実験手順

A 10 mL microwave tube was charged with 3-bromo-N-propyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (0.052 g, 0.2 mmol), K2CO3 (0.14 g, 1.0 mmol), DMF (2 mL), and cyclohexyl chloride (0.072 g, 0.6 mmol). The resulting mixture was heated at 200° C. for 30 minutes under microwave irradiation. After the reaction was cooled to room temperature, phenylboronic acid (0.37 g, 0.3 mmol), Pd(PPh3)4 (0.023 g, 0.02 mmol), and H2O (1 mL) were added sequentially. The mixture was stirred at room temperature for 3 min and then heated at 150° C. for 15 min. After cooled to room temperature, the mixture was partitioned in H2O and Et2O. The aqueous phase was extracted with ether (3×). The combined organic phase were dried (Na2SO4) and concentrated. The residue was purified by Isco to provide the 1-cyclohexyl-3-phenyl-N-propyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine (UNC702A) (0.045 g, 67%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 7.90 (d, J=8.0 Hz, 2H), 7.48 (t, J=6.0 Hz, 2H), 7.38 (t, J=6.0 Hz, 1H), 5.42 (s, 1H), 4.60 (tt, J=11.6, 4.1 Hz, 1H), 3.48 (dt, J=13.1, 6.8 Hz, 2H), 2.18-2.08 (m, 2H), 2.04-2.00 (m, 2H), 1.95-1.92 (m, 2H), 1.77-1.74 (m, 1H), 1.74-1.65 (m, 2H), 1.58-1.42 (m, 2H), 1.40-1.28 (m, 1H), 1.03 (t, J=7.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 160.73, 155.38, 153.50, 143.71, 133.27, 129.06, 128.60, 127.09, 106.91, 56.10, 43.68, 32.16, 25.91, 25.61, 22.98, 11.77; MS m/z 336.2 [M+1].

後処理

  1. temperatureAfter the reaction was cooled to room temperature
  2. temperatureheated at 150° C. for 15 min
  3. temperatureAfter cooled to room temperature
  4. customthe mixture was partitioned in H2O
  5. extractionThe aqueous phase was extracted with ether (3×)
  6. dry with materialThe combined organic phase were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue was purified by Isco

出典と根拠

ORDレコード
ord-a7f2c8f0cacb4db8a4003745e6eadd6e
出典データセット
uspto-grants-2016_03
特許番号
US09290499B2

関連ノート

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