Lithium hydroxide, monohydrate → lithium 1-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indazole-7-carboxylate

HRID 2369937Notes

Reaction equation

HRID 2369937 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][NH:10][CH2:11][CH2:12][N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[C:22]([O:24]C)=[O:23])[CH:15]=[N:14]3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.O.[OH-].[Li+:28]>O1CCCC1.O>[N:1]12[CH2:8][CH2:7][C:4]([CH2:9][NH:10][CH2:11][CH2:12][N:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[C:22]([O-:24])=[O:23])[CH:15]=[N:14]3)([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Li+:28]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66899335methyl 1-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indazole-7-carboxylate

Product 1

HCID 66899618lithium 1-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indazole-7-carboxylateYield 211.1%

Reagents, catalysts & solvents 1

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

Procedure

A mixture of methyl 1-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indazole-7-carboxylate (563 mg, 1.7 mmol) from Step F above and lithium hydroxide monohydrate (207 mg, 4.9 mmol) in tetrahydrofuran/water (16 mL; 1:1) was stirred at reflux until the reaction was complete by TLC and/or LC-MS. The solvent was removed under reduced pressure to give lithium 1-(2-(quinuclidin-4-ylmethylamino)ethyl)-1H-indazole-7-carboxylate (1.20 g, crude): 1H NMR (300 MHz, CD3OD) δ 8.03 (s, 1H), 7.72 (d, J=8.1 Hz, 1H), 7.55 (d, J=7.2 Hz, 1H), 7.11 (t, J=7.4 Hz, 1H), 3.28-3.20 (m, 2H); 2.98 (t, J=6.6 Hz, 2H), 2.81 (t, J=7.5 Hz, 6H), 2.28 (s, 2H), 1.36 (t, J=8.1 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-f92e72b706ba41bcb2bc000d8a8374d8
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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