Acetic Acid → 1446223-96-6

HRID 1477513Notes

Reaction equation

HRID 1477513 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([NH:9][C:10]([C:13]2[NH:14][C:15](=[O:24])[C:16]([OH:23])=[C:17]([C:19]([O:21]C)=O)[N:18]=2)([CH3:12])[CH3:11])=[O:8])=[N:4][N:3]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH2:31])=[CH:28][CH:27]=1.C(O)(=O)C.O>C(O)(C)C>[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30][NH:31][C:19]([C:17]2[N:18]=[C:13]([C:10]([NH:9][C:7]([C:5]3[O:6][C:2]([CH3:1])=[N:3][N:4]=3)=[O:8])([CH3:11])[CH3:12])[NH:14][C:15](=[O:24])[C:16]=2[OH:23])=[O:21])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 673264-FluorobenzylamineHCID 136502909HCID 136502909, compound

Product 1

HCID 1362364801446223-96-6

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82.5 °C

Procedure

Methyl 2-(2-(5-methyl-1,3,4-oxadiazole-2-carboxamido)propan-2-yl)-1,6-dihydro-5-hydroxy-6-oxopyrimidine-4-carboxylate [V(a); 40 gms] was suspended in isopropyl alcohol (400 ml) and 4-fluorobenzyl amine (30 gms) was added to the above mixture. The reaction mixture was stirred at 80 to 85° C. After completion, reaction mass was cooled to 60° C. and acetic acid (1600 ml) and water (400 ml) was added. The resultant crystalline product was filtered and washed with mixture of water and isopropyl alcohol (1:1) and dried to give N-(4-fluorobenzyl)-2-(2-(5-methyl-1,3,4-oxadiazole-2-carboxamido) propan-2-yl)-1,6-dihydro-5-hydroxy-6-oxopyrimidine-4-carboxamide VI).

Workup

  1. customAfter completion, reaction mass
  2. temperaturewas cooled to 60° C.
  3. filtrationThe resultant crystalline product was filtered
  4. washwashed with mixture of water and isopropyl alcohol (1:1)
  5. customdried

Sources & evidence

ORD record
ord-eb85126b9d9e42069b8bc2e30d695765
Source dataset
uspto-grants-2016_08
Patent number
US09403809B2

Reaction notes

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