Triethylamine → HCID 57780718, 화합물

HRID 2076101노트

반응식

HRID 2076101 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19](OS(C)(=O)=O)[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:25]=[CH:24][C:23]3[CH2:22][CH2:21][CH2:20][CH:19]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)[C:18]=3[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 57780691HCID 57780691, 화합물

생성물 1

HCID 57780718HCID 57780718, 화합물수율 42.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of methanesulfonic acid 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-5,6,7,8-tetrahydro-quinazolin-8-yl ester (61 mg, 0.14 mmol) in tetrahydrofurane (1.4 mL) was added under nitrogen at 0° C. pyrrolidine (20 mg, 0.28 mmol) and triethyl amine (29 mg, 0.28 mmol). The reaction was stirred at room temperature over night, heated to reflux for 2 hours. A few drops of dimethylformamide were added and the reaction was stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure, dissolved in water and extracted twice with ethyl acetate. The combined organic layers were washed with dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The residue was purified on silica gel using dichloromethane/methanol/concentrated aqueous ammonia (19:1:0.2 v/v/v) as eluent to yield the title compound (24 mg, 42%) as a yellow solid. MS ISP (m/e): 234.3 (100), 334 (24), 405.3 (69) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.61 (s, 1H), 8.29 (s, 1H), 7.95 (s, 1H), 7.64 (s, 1H), 7.38 (d, 1H), 7.20 (d, 1H), 7.02 (s, 1H), 3.80 (s, 3H), 2.55-2.80 (m, 4H), 2.14 (s, 3H), 2.04 (m, 2H), 1.60-1.80 (m, 6H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. stirringthe reaction was stirred at room temperature for 2 hours
  4. concentrationThe reaction was concentrated under reduced pressure
  5. dissolutiondissolved in water
  6. extractionextracted twice with ethyl acetate
  7. washThe combined organic layers were washed
  8. dry with materialwith dried over sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customThe residue was purified on silica gel

출처 및 근거

ORD 기록
ord-2111b946c97d4811b61546745c32718f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923450B2

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