Potassium Carbonate → 3-({[2-(3-Fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 219679Notes

Reaction equation

HRID 219679 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][NH2:21])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].[F:22][C:23]1[CH:24]=[C:25]([C:29]2[N:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][N:30]=2)[CH:26]=[CH:27][CH:28]=1>C(OCC)(=O)C.O>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][NH:21][C:35]([C:32]2[CH:33]=[N:34][C:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)=[N:30][CH:31]=2)=[O:36])[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of potassium carbonate (13.94 mmol) and 3-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (4.65 mmol) in ethyl acetate (30 mL) and water (20 mL) is added a solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (4.65 mmol) in ethyl acetate (20 mL). The mixture is stirred at room temperature overnight. The reaction mixture is extracted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated in vacuo to give 3-({[2-(3-fluoro-phenyl)-pyrimidine-5-carbonyl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a solid. MS 415 (M+H); 1H NMR (300 MHz, CDCl3): δ 1.47 (s, 9H), 1.55-2.22 (m, 5H), 2.90-4.90 (m, 6H), 7.15-7.25 (m, H), 7.41-7.53 (m, H), 7.56 (bs, NH), 8.18 (d, H), 8.29 (d, H), 9.21 (s, 2H).

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac93448d500f452fb611ba6bd1fd101d
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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