Diisopropylethylamine → HCID 86661469, compound

HRID 1942961Notes

Reaction equation

HRID 1942961 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[N:5]=[C:4]([NH:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[N:3]=1.CCN(C(C)C)C(C)C.[NH2:39][CH2:40][C:41]1[CH:42]=[CH:43][C:44]([Cl:47])=[N:45][CH:46]=1>O1CCOCC1.C(Cl)(Cl)Cl>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[C:6]1[N:5]=[C:4]([NH:16][N:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=2)[N:3]=[C:2]([NH:39][CH2:40][C:41]2[CH:46]=[N:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 86661470HCID 86661470, compound

Product 1

HCID 86661469HCID 86661469, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 2-chloro-4-(2-chloro-6-fluorophenyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazine (XVII) (250 mg, 0.56 mmol) in 1,4-dioxane (2 mL) was treated with a solution of iPr2NEt (144.8 mg, 1.12 mmol) in 1,4-dioxane (1 mL). The mixture was treated with a solution of 5-aminomethyl-2-chloropyridine (80.37 mg, 0.564 mmol) in 1,4-dioxane (1 mL). The reaction was stirred overnight at room temperature. The reaction was concentrated on a rotary evaporator and the residue was taken up in ethyl acetate and washed with brine. The aqueous layer was extracted twice with ethyl acetate. The combined organics was dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to yield a white solid. The solid was taken up in chloroform and loaded onto 100 g of silica gel. The silica gel was eluted with ethyl acetate/hexanes (30%, 40%, 50%, 70%). The appropriate fractions were concentrated on a rotary evaporator to yield 4-(2-chloro-6-fluorophenyl)-N-((6-chloropyridin-3-yl)methyl)-6-(2-(4-(trifluoromethoxy)benzylidene)hydrazinyl)-1,3,5-triazin-2-amine (Example 22) as a white solid (305 mg). ESI/MS 552.3, 554.2 (M+H), 550.4, 552.4 (M−H).

Workup

  1. concentrationThe reaction was concentrated on a rotary evaporator
  2. washwashed with brine
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialThe combined organics was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator
  7. customto yield a white solid
  8. washThe silica gel was eluted with ethyl acetate/hexanes (30%, 40%, 50%, 70%)
  9. concentrationThe appropriate fractions were concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-506bcb0cf9b14f739fb09fc228b71db7
Source dataset
uspto-grants-2013_03
Patent number
US08389718B2

Reaction notes

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