Sodium Carbonate → HCID 71086859, 화합물

HRID 571828노트

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HRID 571828 반응식
[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]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 167023-AminobenzonitrileHCID 94429TriphosgeneHCID 86674686HCID 86674686, 화합물

생성물 1

HCID 71086859HCID 71086859, 화합물수율 42.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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]+).

후처리

  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)

출처 및 근거

ORD 기록
ord-95ecaefb4cfd4daea11844f12515143e
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029370B2

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