Lithium hydroxide, monohydrate → HCID 66899372, compound

HRID 2369883Notes

Reaction equation

HRID 2369883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=1)[N:7]([CH2:15][CH2:16][NH:17][C@H:18]1[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]1)[N:6]=[CH:5]2.O.[OH-].[Li+:28]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O-:13])=[O:12])[CH:10]=1)[N:7]([CH2:15][CH2:16][NH:17][C@H:18]1[CH:23]3[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]3)[CH2:19]1)[N:6]=[CH:5]2.[Li+:28]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66899017HCID 66899017, compound

Product 1

HCID 66899372HCID 66899372, compoundYield 120.5%

Reagents, catalysts & solvents 1

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

Procedure

A mixture of (S)-methyl 5-chloro-1-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-7-carboxylate (525 mg, 1.5 mmol) from Step D above and lithium hydroxide monohydrate (183 mg, 4.4 mmol) in tetrahydrofuran/water (14 mL, 1:1) was stirred at room temperature until the reaction was complete by TLC (2-3 h). The solvent was removed under reduced pressure to give lithium (S)-5-chloro-1-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-7-carboxylate as a green solid (641 mg, 100%): 1H NMR (300 MHz, CD3OD) δ 8.01 (s, 1H), 7.71 (s, 1H), 7.48 (s, 1H), 4.80 (t, J=6.6 Hz, 2H), 3.10-2.96 (m, 2H), 2.95-2.88 (m, 1H), 2.80-2.58 (m, 5H), 2.33-2.27 (m, 1H), 1.80-1.76 (m, 1H), 1.72-1.60 (m, 2H), 1.60-1.40 (m, 1H), 1.40-1.20 (m, 2H); MS (ESI+) m/z 349 (M+H).

Workup

  1. customwas complete by TLC (2-3 h)
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6c2698cdb2344920bcf7b1d01582e4dc
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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