Piperidine → HCID 57780682、化合物

HRID 2076103ノート

反応式

HRID 2076103 の反応式
[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[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>CN(C)C=O.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[CH2:36][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

参加物

6

反応物 3

HCID 8082Piperidine2 回HCID 8471TriethylamineHCID 57780691HCID 57780691、化合物

生成物 1

HCID 57780682HCID 57780682、化合物収率 18%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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 (76 mg, 0.18 mmol) in dimethylformamide (2 mL) was added under nitrogen at 0° C. piperidine (30 mg, 0.35 mmol) and triethyl amine (36 mg, 0.35 mmol). The reaction was stirred at room temperature over night. Piperidine (30 mg, 0.35 mmol) was added and the reaction stirred at room temperature for 3 hours. The reaction was diluted with water and extracted twice with diethyl ether. 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 (13 mg, 18%) as an orange solid. MS ISP (m/e): 334.3 (27), 419.3 (100) [(M+H)+]. 1H NMR (DMSO-D6, 300 MHz): δ (ppm)=9.60 (s, 1H), 8.26 (s, 1H), 7.82 (s, 1H), 7.65 (s, 1H), 7.60 (d, 1H), 7.19 (d, 1H), 7.03 (s, 1H), 3.80 (s, 3H), 3.63 (m, 1H), 3.05 (m, 1H), 2.55-2.80 (m, 2H), 2.25 (m, 2H), 2.14 (s, 3H), 1.89 (m, 2H), 1.38-1.68 (m, 8H).

後処理

  1. stirringthe reaction stirred at room temperature for 3 hours
  2. extractionextracted twice with diethyl ether
  3. washThe combined organic layers were washed
  4. dry with materialwith dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified on silica gel

出典と根拠

ORDレコード
ord-224149137b5b47dc979f0e3a4431214d
出典データセット
uspto-grants-2011_04
特許番号
US07923450B2

反応ノート

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