Sodium Hydroxide → HCID 178524333, compound

HRID 1349880Notes

Reaction equation

HRID 1349880 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:41]=[C:42]([CH:47]=[CH:48][CH:49]=2)[C:43]([O:45]C)=[O:44])=[N:8]1.[OH-].[Na+]>CO>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:41]=[C:42]([CH:47]=[CH:48][CH:49]=2)[C:43]([OH:45])=[O:44])=[N:17]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22479977HCID 22479977, compound

Product 1

HCID 178524333HCID 178524333, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared using methyl 3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}benzoate (0.125 g, 0.19 mmol), 6 N sodium hydroxide (aqueous) (3 mL), and methanol (3 mL) heated at 60° C. for 6 hours. The reaction was allowed to cool to room temperature, and extracted with diethyl ether (2×). The aqueous fraction was dropwise added to a 6 N hydrochloride solution (aqueous) to form a white precipitate, which is filtered and dried in a vacuum oven (0.018 g, 30% yield): 1H NMR (DMSO-d6) δ 8.91 (m, 2H), 8.60 (s, 1H), 8.36 (d, 1H), 8.16 (d, 1H), 8.02 (d, 1H), 7.75 (m, 2H); ES-MS (m/z) 306 [M+1]+.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (2×)
  3. additionThe aqueous fraction was dropwise added to a 6 N hydrochloride solution (aqueous)
  4. customto form a white precipitate, which
  5. filtrationis filtered
  6. customdried in a vacuum oven (0.018 g, 30% yield)

Sources & evidence

ORD record
ord-b6d903f8a6ee4431bdcd309e0d3b36d1
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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