Tetrahydrofuran → HCID 58156091, compound

HRID 408767Notes

Reaction equation

HRID 408767 reaction equation
O[Li].O.C([O:6][C:7]([C:9]1[CH:10]=[N:11][N:12]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([Cl:25])[C:21]([Cl:24])=[C:22]([Br:23])[C:16]=3[N:15]=2)[CH:13]=1)=[O:8])C.C1COCC1>O>[Br:23][C:22]1[C:16]2[N:15]=[C:14]([N:12]3[CH:13]=[C:9]([C:7]([OH:8])=[O:6])[CH:10]=[N:11]3)[NH:18][C:17]=2[CH:19]=[C:20]([Cl:25])[C:21]=1[Cl:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66937225HCID 66937225, compound

Product 1

HCID 58156091HCID 58156091, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

LiOH.H2O (0.046 g, 1.09 mmol) was added to a mixture of 1-(4-Bromo-5,6-dichloro-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.088 g, 0.22 mmol), THF (1 mL), and water (0.33 mL), and the mixture was stirred 18 h at 23° C. The solvent was evaporated, water (3 mL) was added and the mixture acidified with 1M HCl. The resulting white precipitate was filtered and dried to yield the titled compound (0.068 g, 83%). MS (ESI/CI): mass calcd. for C11H6BrCl2N4O2, 374.9; m/z found, 375.9 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.89 (s, 1H), 8.32 (s, 1H), 7.74 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. additionwater (3 mL) was added
  3. filtrationThe resulting white precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-766725d001744643ac2e4411bef27c0e
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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