Ethyl Acetate → HCID 58964357, compound

HRID 2039724Notes

Reaction equation

HRID 2039724 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH2:9][C@H:10]([CH3:19])[C:11]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[O:12].C(OCC)(=O)C>C1COCC1.C(O)(C)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:9][C@H:10]([CH3:19])[C:11]([NH:13][CH2:14][C:15]([F:16])([F:17])[F:18])=[O:12])[N:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 178102,4-Dichloro-1,3,5-triazineHCID 28172280HCID 28172280, compound

Product 1

HCID 58964357HCID 58964357, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2,4-dichloro-1,3,5-triazine (298 mg, 2.0 mmol) in 4 mL THF and isopropanol(1:1 v:v) at −20° C. was added (R)-2-amino-N-(2,2,2-trifluoroethyl)propanamide (412 mg, 2.0 mmol, 1.0 equiv.), followed by the addition of N,N-isopropyl ethyl amine (516 mg, 4.0 mmol, 2.0 equiv.). The reaction was stirred at −20° C. for 20 minutes then was allowed to warm to room temperature. After 30 minutes, the reaction was poured into ethyl acetate and washed with water. The organic layer was concentrated. The oily residue was purified by chromatography (2:1 hexane/ethyl acetate) to produce 186 mg of (R)-2-(4-chloro-1,3,5-triazin-2-ylamino)-N-(2,2,2-trifluoroethyl)propanamide (compound 1034) (LC/MS: MS+1=284.1, MS−1=282.3, R.T.=1.5 min).

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 30 minutes
  3. washwashed with water
  4. concentrationThe organic layer was concentrated
  5. customThe oily residue was purified by chromatography (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-90478b29382645c7938a443e00c471c4
Source dataset
uspto-grants-2013_11
Patent number
US08580802B2

Reaction notes

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