Diisopropylethylamine → 2-[(3-chloro-1,2,4-triazin-5-yl)amino]-2-methyl-N-(2,2,2-trifluoroethyl) propanamide

HRID 510188Notes

Reaction equation

HRID 510188 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[N:7]=1.Cl.[NH2:10][C:11]([CH3:21])([CH3:20])[C:12]([NH:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[O:13].C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>ClCCl.O1CCOCC1>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([NH:10][C:11]([CH3:21])([CH3:20])[C:12]([NH:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[O:13])[N:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 122649333,5-Dichloro-1,2,4-triazineHCID 877733842-Amino-2-methyl-N-(2,2,2-trifluoro-ethyl)-propionamide; hydrochloride

Product 1

HCID 894954772-[(3-chloro-1,2,4-triazin-5-yl)amino]-2-methyl-N-(2,2,2-trifluoroethyl) propanamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a Dioxane (12.0 ml) solution of 3,5-dichloro-1,2,4-triazine I-15a (846 mg, 5.64 mmol) was added 2-amino-2-methyl-N-(2,2,2-trifluoroethyl) propanamide hydrochloride (1,242 mg, 5.64 mmol) followed by diisopropylethylamine (2.96 ml, 16.92 mmol). Dichloromethane (2 mL) was added and the reaction stirred for 2 hours at room temp. The reaction was diluted with dichloromethane and poured into saturated sodium bicarbonate. A precipitate formed. The solid was filtered washed with dichloromethane and then dried under reduced pressure to afford the product I-15 (1.02 g, 60.3%). LRMS (ESI) m/z 297.9 [(M+H)+; calcd for: C9H11ClF3N5O: 298.1].

Workup

  1. customA precipitate formed
  2. filtrationThe solid was filtered
  3. washwashed with dichloromethane
  4. customdried under reduced pressure
  5. customto afford the product I-15 (1.02 g, 60.3%)

Sources & evidence

ORD record
ord-70b6eabfe949404090863454be95e349
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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