Lithium hydroxide, monohydrate → HCID 66772490, compound

HRID 2370329Notes

Reaction equation

HRID 2370329 reaction equation
C1CCN(CCCN2CC3C4C=CC(F)=CC=4C(NC=3CC2)=O)CC1.[CH2:26]([N:33]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([C:42]([O:44]C)=[O:43])[C:36]=2[C:35]([CH2:46][CH2:47][NH:48][C@@H:49]2[CH:54]3[CH2:55][CH2:56][N:51]([CH2:52][CH2:53]3)[CH2:50]2)=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O.[OH-].[Li+:59]>>[CH2:26]([N:33]1[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([C:42]([O-:44])=[O:43])[C:36]=2[C:35]([CH2:46][CH2:47][NH:48][C@@H:49]2[CH:54]3[CH2:55][CH2:56][N:51]([CH2:52][CH2:53]3)[CH2:50]2)=[N:34]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1.[Li+:59]

Participants

4

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 66772162HCID 66772162, compoundHCID 74892009HCID 74892009, compound

Product 1

HCID 66772490HCID 66772490, compoundYield 101%

Procedure

Following general procedure GP-L, (R)-methyl 1-benzyl-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate (1.1 mg, 2.63 mmol) and lithium hydroxide monohydrate (332 mg, 7.89 mmol) were converted lithium (R)-1-benzyl-3-(2-(quinuclidin-3-ylamino)ethyl)-1H-indazole-4-carboxylate (1.09 g, quant. yield) which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 7.37-7.34 (m, 1H), 7.30-7.26 (m, 3H), 7.25-7.11 (m, 3H), 7.06-7.03 (m, 1H), 5.54 (s, 2H), 3.27 (m, 2H), 2.85-2.70 (m, 4H), 2.67-2.50 (m, 3H), 2.18-2.12 (m, 1H), 1.75-1.45 (m, 3H), 1.40-1.15 (m, 2H): MS (ESI+) m/z 405 (M+H).

Sources & evidence

ORD record
ord-b3b8c1a86b724ab9b6b5ce2006e23d63
Source dataset
uspto-grants-2014_04
Patent number
US08710047B2

Reaction notes

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