Lithium hydroxide, monohydrate → HCID 178524261, compound

HRID 2369928Notes

Reaction equation

HRID 2369928 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][NH:10][CH2:11][C:12]3[C:20]4[C:19]([C:21]([O:23]C)=[O:22])=[CH:18][CH:17]=[CH:16][C:15]=4[NH:14][N:13]=3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.O.[OH-].[Li+:27]>O1CCCC1.O>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][NH:10][CH2:11][C:12]3[C:20]4[C:19]([C:21]([O-:23])=[O:22])=[CH:18][CH:17]=[CH:16][C:15]=4[NH:14][N:13]=3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Li+:27]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178497598HCID 178497598, compound

Product 1

HCID 178524261HCID 178524261, compoundYield 136.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of methyl 3-((quinuclidin-4-ylmethylamino)methyl)-1H-indazole-4-carboxylate (2.9 g, 8.9 mmol) from Step A above and lithium hydroxide monohydrate (1.1 g, 26.7 mmol) in tetrahydrofuran/water (1:1, 30 mL) was stirred at reflux until the reaction was complete by LC-MS. The solvent was removed under reduced pressure to give lithium 3-((quinuclidin-4-ylmethylamino)methyl)-1H-indazole-4-carboxylate as a brown solid (3.9 g, quantitative yield): 1H NMR (500 MHz, CD3OD) δ 7.49 (d, J=8.5 Hz, 1H), 7.43 (d, J=7.0 Hz, 1H), 7.35 (t, J=8.0 Hz, 1H), 4.17 (s, 2H), 2.82 (t, J=8.0 Hz, 6H), 2.26 (s, 2H), 1.42 (t, J=8.0 Hz, 6H); MS (ESI+) m/z 315 (M+H).

Workup

  1. temperatureat reflux until the reaction
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9d2ebfbb4979476198f4e5c91b971598
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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