Triethylamine → 2-Chloro trifluoromethyl-pyrimidin-5-carboxylic acid (cyclopentylmethyl)-amide

HRID 1868383Notes

Reaction equation

HRID 1868383 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([C:12](Cl)=[O:13])=[CH:4][N:3]=1.Cl.[CH:16]1([CH2:21][NH2:22])[CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C>ClCCl>[CH:16]1([CH2:21][NH:22][C:12]([C:5]2[C:6]([C:8]([F:11])([F:10])[F:9])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=2)=[O:13])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27367082-Chloro-4-(trifluoromethyl)pyrimidine-5-carbonyl chlorideHCID 18784136Cyclopentylmethanamine hydrochloride

Product 1

HCID 579826072-Chloro trifluoromethyl-pyrimidin-5-carboxylic acid (cyclopentylmethyl)-amideYield 67.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-chloro-4-trifluoromethyl-pyrimidin-5-carbonyl chloride (1.0 g, ex Maybridge) in dichloromethane (7 ml) at −2° was added a dropwise a solution of cyclopentanemethanamine hydrochloride (0.55 g) and triethylamine (1.4 ml) in dichloromethane (13 ml) and the solution stirred at 0° for 1 hour. Dichloromethane was removed under reduced pressure and ethyl acetate (20 ml) added. The solution was washed with 2N hydrochloric acid (3×15 ml), dried (MgSO4), evaporated and triturated with isohexane to afford 2-chloro trifluoromethyl-pyrimidin-5-carboxylic acid (cyclopentylmethyl)-amide (838 mg).

Workup

  1. customDichloromethane was removed under reduced pressure and ethyl acetate (20 ml)
  2. additionadded
  3. washThe solution was washed with 2N hydrochloric acid (3×15 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customtriturated with isohexane

Sources & evidence

ORD record
ord-4fbb2425a7f141d7b950b33005b25226
Source dataset
uspto-grants-2009_12
Patent number
US07635701B2

Reaction notes

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