Tetrahydrofuran → HCID 58156091, compound

HRID 538199Notes

Reaction equation

HRID 538199 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-f660a561cd334e4f8b5f5e2eacf5d6bd
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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