1,4-Dioxane hydrochloride → 3-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine, dihydrochloride salt

HRID 446745Notes

Reaction equation

HRID 446745 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[C:26]1[N:30]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([F:39])[C:32]=2[F:40])[N:29]=[N:28][N:27]=1.[ClH:41].O1CCOCC1>>[ClH:41].[ClH:41].[F:40][C:32]1[C:33]([F:39])=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:31]=1[N:30]1[C:26]([C:3]2[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]3[CH:9]=[N:10][N:11]([CH:13]4[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]4)[CH:12]=3)[CH:4]=2)=[N:27][N:28]=[N:29]1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58293836tert-butyl 4-(4-(6-amino-5-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 1317307013-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine, dihydrochloride saltYield 98.2%

Procedure

Compound 1103 (3.0 g, 5.419 mmol) was treated with 4 M HCl/dioxane (50 mL, 200.0 mmol) for 1 hour at RT. The solvents were removed by vacuum evaporation to give 3-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)-5-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)pyridin-2-amine, dihydrochloride salt (Compound 12, 2.8 g, 98%) as a slightly yellow solid.

Workup

  1. customThe solvents were removed by vacuum evaporation

Sources & evidence

ORD record
ord-594ae4dbf4264d50b9f94e6c1b85cd12
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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