Water → HCID 66772189, compound

HRID 1887517Notes

Reaction equation

HRID 1887517 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19]C)=[O:18])[C:11]=3[C:10]([CH2:21][NH:22][C@@H:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[N:9]2)=[CH:4][CH:3]=1.O.O.[OH-].[Li+:34]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O-:19])=[O:18])[C:11]=3[C:10]([CH2:21][NH:22][C@@H:23]3[CH:28]4[CH2:27][CH2:26][N:25]([CH2:30][CH2:29]4)[CH2:24]3)=[N:9]2)=[CH:4][CH:3]=1.[Li+:34]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66772970HCID 66772970, compound

Product 1

HCID 66772189HCID 66772189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 1-(4-fluorophenyl)-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate (492 mg, 1.2 mmol) from Step B above in THF (2.5 mL) and H2O (2.5 ml) was added lithium hydroxide monohydrate (152 mg, 3.6 mmol). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue was dried overnight under vacuum to afford crude lithium (R)-1-(4-fluorophenyl)-3-((quinuclidin-3-ylamino)methyl)-1H-indazole-4-carboxylate which was used in the next step without further purification; MS (ESI+) m/s 394 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was dried overnight under vacuum

Sources & evidence

ORD record
ord-47a7945fcd434f9498d47ff7cfef432a
Source dataset
uspto-grants-2013_08
Patent number
US08501729B2

Reaction notes

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