Triethylamine → Tert-butyl 4-(2-(2-chloro-5-((2,6-dichlorophenyl)carbamoyl)pyrimidin-4-ylhydrazinyl)ethyl)piperidine-1-carboxylate

HRID 2357992Notes

Reaction equation

HRID 2357992 reaction equation
[NH:1]([CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[NH2:2].[Cl:18][C:19]1[N:24]=[C:23](Cl)[C:22]([C:26]([NH:28][C:29]2[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:36])=[O:27])=[CH:21][N:20]=1.C(N(CC)CC)C>C1COCC1>[Cl:18][C:19]1[N:20]=[C:21]([NH:2][NH:1][CH2:3][CH2:4][CH:5]2[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]2)[C:22]([C:26](=[O:27])[NH:28][C:29]2[C:30]([Cl:36])=[CH:31][CH:32]=[CH:33][C:34]=2[Cl:35])=[CH:23][N:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 59389577Tert-butyl 4-(2-hydrazinylethyl)piperidine-1-carboxylateHCID 729421582,4-Dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide

Product 1

HCID 86611603Tert-butyl 4-(2-(2-chloro-5-((2,6-dichlorophenyl)carbamoyl)pyrimidin-4-ylhydrazinyl)ethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 618 mg (2.5 mmol) of tert-butyl 4-(2-hydrazinylethyl)piperidine-1-carboxylate in 10 mL THF was cooled to 0° C. and treated sequentially with 763 mg (2.3 mmol) of 2,4-dichloro-N-(2,6-dichlorophenyl)pyrimidine-5-carboxamide and 355 μl (2.5 mmol) of triethylamine. The resulting yellow slurry was warmed to room temperature and stirred for 66 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (CH2Cl2:MeOH, 99.5:0.5 grading to CH2Cl2:MeOH, 98:2) to give the title compound 92. 1H-NMR (CDCl3) δ 1.08-1.23 (m, 3H), 1.45 (s, 9H), 1.58-1.66 (m, 2H), 1.72-1.79 (m, 2H), 2.61-2.75 (m, 2H), 3.87 (t, J=7.1 Hz, 2H), 3.99-4.14 (m, 4H), 7.24 (t, J=8.4 Hz, 1H), 7.43 (d, J=8.1 Hz, 2H), 7.48 (s, 1H), 8.40 (s, 1H). Mass Spectrum (ESI) m/e=543.1 (M+1).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL)
  2. extractionextracted with CH2Cl2 (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe filtrate was purified by chromatography on silica gel (CH2Cl2:MeOH, 99.5:0.5 grading to CH2Cl2:MeOH, 98:2)

Sources & evidence

ORD record
ord-850870c833df440c9bc6b48ed3532065
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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