1,2-Dichloroethane → 3-Benzyl-7-chloro-1-pyrrolidine-2-yl-2,3-dihydro-1H-quinazoline-4-one

HRID 225769

反応式

HRID 225769 の反応式
[CH2:1](Cl)[CH2:2]Cl.[CH:5]([N:8](C(C)C)CC)(C)[CH3:6].C(N)C1C=CC=CC=1.C(OC(N1CCCC1[C:34](=O)[NH:35][C:36]1[CH:41]=C(Cl)[CH:39]=[CH:38][C:37]=1[C:43](=[O:52])[NH:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=O)(C)(C)C.Cl[CH2:55][Cl:56]>>[CH2:45]([N:44]1[C:43](=[O:52])[C:37]2[C:36](=[CH:41][C:55]([Cl:56])=[CH:39][CH:38]=2)[N:35]([CH:2]2[CH2:1][CH2:6][CH2:5][NH:8]2)[CH2:34]1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

参加物

6

反応物 5

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 866092512-(2-Benzylcarbamoyl-5-chloro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 690643443-Benzyl-7-chloro-1-pyrrolidine-2-yl-2,3-dihydro-1H-quinazoline-4-one収率 88%

実験手順

To a solution of the compound of Formula 104 (8.7 9, 24 mmol) in dichloromethane (250 mL) was added EDC (14.85 g, 77 mmol), and diisopropylethylamine (14.1 mL, 81 mmol). After stirring at room temperature for 1.5 hours, benzylamine (8.4 mL, 77 mmol) was added and the reaction stirred for an additional 48 hours. The mixture was washed with water (2×50 mL), 10% phosphoric acid (2×50 mL), and saturated NaHCO3 (50 mL). The organic phase was dried over MgSO4, filtered and concentrated under vacuum to give a mixture of 9.4 g (88% yield) of the desired product of Formula 105, 2-(2-benzylcarbamoyl-5-chloro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, as a light yellow foam, together with a small amount of 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-2Hquinzoline-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (Formula 106), which was taken on without further purification. LRMS (MH+) m/z 458.

後処理

  1. stirringthe reaction stirred for an additional 48 hours
  2. washThe mixture was washed with water (2×50 mL), 10% phosphoric acid (2×50 mL), and saturated NaHCO3 (50 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give

出典と根拠

ORDレコード
ord-924983f59a61409b9a502dc7aa2b72b5
出典データセット
uspto-grants-2009_07
特許番号
US07557115B2

関連ノート

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