Hydrochloric Acid → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (piperidin-3-ylmethyl)-amide hydrochloride

HRID 219680Notes

Reaction equation

HRID 219680 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][NH:16][C:17]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[N:23][CH:24]=2)=[O:18])[CH2:10]1)=O)(C)(C)C>C(Cl)Cl>[ClH:1].[NH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][NH:16][C:17]([C:19]2[CH:24]=[N:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[N:21][CH:20]=2)=[O:18])[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 691635173-({[2-(3-Fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 866232202-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (piperidin-3-ylmethyl)-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas is bubbled into a solution of 3-({[2-(3-fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (3.76 mmol) in DCM (20 mL) and the reaction is stirred at room temperature for 2 hours. The mixture is concentrated in vacuo to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (piperidin-3-ylmethyl)-amide hydrochloride as a solid. MS 415 (M+H); 1H NMR (300 MHz, CD3OD): δ 1.22-1.50 (m, 2H), 1.68-1.90 (m, H), 1.90-2.06 (bs, 2H), 2.06-2.17 (bs, 6H), 2.73-3.04 (m, 2H), 3.24-3.50 (m, H), 7.24-7.35 (m, H), 7.48-7.60 (m, H), 8.19 (d, H), 8.34 (d, H), 9.23 (s, 2H).

Workup

  1. concentrationThe mixture is concentrated in vacuo

Sources & evidence

ORD record
ord-5b69e1f7299144d3a4bc120931af7da9
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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