Tetrahydrofuran → HCID 178524818, compound

HRID 1521399Notes

Reaction equation

HRID 1521399 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]([Cl:30])[C:18]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)(=[O:22])=[O:21])=[CH:19][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.C1COCC1.O[Li].O>O>[Cl:30][C:17]1[C:18]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:19][C:13]2[N:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)[NH:15][C:14]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178469990HCID 178469990, compound

Product 1

HCID 178524818HCID 178524818, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a mixture of 1-[6-chloro-5-(4-chloro-benzenesulfonyl)-1H-benzoimidazol-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (1.92 g, 4.13 mmol), THF (16 mL), and water (5 mL) was added LiOH.H2O (0.693 g, 16.5 mmol). The mixture was stirred for 18 h at 23° C. The solvent was evaporated, water (10 mL) was added and the mixture acidified with 1M HCl. The resulting precipitate was filtered and dried to yield the titled compound (1.73 g, 94%). MS (ESI/CI): mass calcd. for C17H10Cl2N4O4S, 436.0; m/z found, 437.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.89 (s, 1H), 8.40 (s, 1H), 8.25 (s, 1H), 7.93-7.90 (m, 2H), 7.69-7.66 (m, 3H).

Workup

  1. customThe solvent was evaporated
  2. additionwater (10 mL) was added
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-972f7ea970a94b32a5796ea944b31d45
Source dataset
uspto-grants-2015_07
Patent number
US09073923B2

Reaction notes

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