Sodium Carbonate → HCID 71086859、化合物

HRID 571828ノート

反応式

HRID 571828 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[C:21]#[N:22].ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].[NH2:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][CH:49]=1)[C:45]#[N:46]>ClCCl.O>[C:17]([O:16][C:14]([N:10]1[CH2:11][CH2:12][O:13][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:27]([NH:41][C:42]3[CH:49]=[CH:48][CH:47]=[C:44]([C:45]#[N:46])[CH:43]=3)=[O:33])=[C:3]([C:21]#[N:22])[CH:4]=2)[CH2:9]1)=[O:15])([CH3:19])([CH3:18])[CH3:20]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 167023-AminobenzonitrileHCID 94429TriphosgeneHCID 86674686HCID 86674686、化合物

生成物 1

HCID 71086859HCID 71086859、化合物収率 42.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of tert-butyl (RS)-2-(4-amino-3-cyanophenyl)morpholine-4-carboxylate (70 mg, example 28b) in dichloromethane (2 ml) was added triphosgene (25 mg). A solution of sodium carbonate (49 mg) in water (2 ml) was then added. The reaction mixture was stirred at room temperature for 3 hours. TLC showed all the starting material had reacted. 3-Aminobenzonitrile (28 mg, CAS 2237-30-1) was then added and the reaction mixture was stirred at room temperature for a further 40 hours. TLC showed the reaction was complete. The reaction mixture was poured into dichloromethane and extracted with water. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: 0% to 100% EtOAc in hexanes) to give (RS)-2-{3-cyano-4-[3-(3-cyano-phenyl)-ureido]-phenyl}-morpholine-4-carboxylic acid tert-butyl ester (16 mg, 16%) as a white solid. MS (ISP): 392.2 ([M+H—C4H8]+), 348.2 ([M+H—C4H8—CO2]+).

後処理

  1. customhad reacted
  2. stirringthe reaction mixture was stirred at room temperature for a further 40 hours
  3. extractionextracted with water
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (SiO2; gradient: 0% to 100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-95ecaefb4cfd4daea11844f12515143e
出典データセット
uspto-grants-2015_05
特許番号
US09029370B2

反応ノート

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