Ammonia → HCID 178522053, compound

HRID 2421499Notes

Reaction equation

HRID 2421499 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:11][C:12]1[C:17]2[NH:18][C:19]([C:21]3[C:22](=[O:37])[NH:23][CH:24]=[CH:25][C:26]=3[NH:27][CH2:28][C@@H:29]([OH:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:20][C:16]=2[CH:15]=[CH:14][CH:13]=1.N>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[C:17]3[NH:18][C:19]([C:21]4[C:22](=[O:37])[NH:23][CH:24]=[CH:25][C:26]=4[NH:27][CH2:28][C@@H:29]([OH:36])[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[N:20][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1230643-Fluorophenyl isocyanateHCID 178507439HCID 178507439, compound

Product 1

HCID 178522053HCID 178522053, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Fluorophenylisocyanate (0.023 g, 0.166 mmol) was added to a solution of 3-(7-amino-1H-benzoimidazol-2-yl)-4-((S)-2-hydroxy-2-phenyl-ethylamino)-1H-pyridin-2-one (0.060 g, 0.166 mmol) (Prepared according to the general method for the intermediates of formula II and III above) in DCM (4 ml) and the reaction stirred at room temperature. After 20 hours methanolic ammonia was added (5 ml) and the reaction stirred for a further 20 hours. The reaction mixture was concentrated under reduced pressure and the crude solid washed with acetonitrile:water (1:1; 10 ml) to give the desired product (0.037 g; 45%).

Workup

  1. customPrepared
  2. stirringthe reaction stirred for a further 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe crude solid washed with acetonitrile:water (1:1; 10 ml)

Sources & evidence

ORD record
ord-f6197dfc2b494b01b8aba00860be7f57
Source dataset
uspto-grants-2011_06
Patent number
US07956190B2

Reaction notes

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