Sodium Carbonate → HCID 71086859, compound

HRID 571828Notes

Reaction equation

HRID 571828 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 71086859HCID 71086859, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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]+).

Workup

  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)

Sources & evidence

ORD record
ord-95ecaefb4cfd4daea11844f12515143e
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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