Triethylamine → Benzyl(1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate

HRID 2079349ノート

反応式

HRID 2079349 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1.Cl.[NH:21]1[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:22]1.C(N(CC)CC)C>C(Cl)Cl>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:4]1[N:3]=[C:2]([N:21]2[CH2:26][CH2:25][CH2:24][CH:23]([CH2:27][NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:22]2)[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 22350243HCID 22350243、化合物HCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

生成物 1

HCID 136121399Benzyl(1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate収率 66%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

2-(4-Chloro-7-methylquinazolin-2-yl)phenol (1.5 g, 5.54 mmol) was suspended in anhydrous CH2Cl2 (15 μL) and cooled to 0° C. under an N2 atmosphere. A mixture of benzyl (piperidin-3-yl)methylcarbamate hydrochloride (1.73 g, 6.09 mmol) in CH2Cl2 (20 mL), and triethylamine (23 mL, 16.67 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature, and the reaction was complete after one hour. It was then partitioned between CH2Cl2/H2O, and separated, and the organic phase was dried over Na2SO4, filtered, and concentrated to an orange solid. Purification by silica gel chromatography using 98% CH2Cl2/2% EtOAc gave benzyl (1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-yl)methylcarbamate as a bright yellow solid (1.75 g, 66%). LC/MS: m/z 483.5 (M+H)+ at 2.81 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

後処理

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. customIt was then partitioned between CH2Cl2/H2O
  4. customseparated
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to an orange solid
  8. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-4222c3ee76ab442c8c8b0a9de6fefec6
出典データセット
uspto-grants-2011_04
特許番号
US07928107B2

反応ノート

読み込み中…