Tetrahydrofuran → HCID 44480583, compound

HRID 538165Notes

Reaction equation

HRID 538165 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]([S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[C:18]([Cl:20])=[CH:19][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.C1COCC1.O[Li].O>O>[Cl:20][C:18]1[C:17]([S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:16][C:14]2[NH:15][C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[N:12][C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66937416HCID 66937416, compound

Product 1

HCID 44480583HCID 44480583, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 1-[5-chloro-6-(propane-2-sulfonyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.179 mg, 0.451 mmol), THF (1.7 mL), and water (0.55 mL) was added LiOH.H2O (56.8 mg, 1.35 mmol). The mixture was sonicated briefly, and stirred at 23° C. for 56 h. The solvent was evaporated, water was added, and the resulting solution was acidified to pH 1 with 1M aq. HCl. The precipitate was collected to yield the titled compound (0.146 g, 86% yield). MS (ESI/CI): mass calcd. for C14H13ClN4O4S, 368.0; m/z found, 369.0 [M+H]+. 1H NMR (600 MHz, DMSO-d6, tautomeric broadening): 14.07 (s, 1H), 13.03 (s, 1H), 8.95 (d, J=0.4 Hz, 1H), 8.36 (s, 1H), 8.16 (s, 1H), 8.09-7.64 (m, 1H), 3.88-3.76 (m, 1H), 1.22 (d, J=7.9 Hz, 6H).

Workup

  1. customThe mixture was sonicated briefly
  2. customThe solvent was evaporated
  3. additionwater was added
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-be70fe809502430b9de6c5a0ab063caa
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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