2,6-Lutidine → HCID 69016944, compound

HRID 1774132Notes

Reaction equation

HRID 1774132 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:8]=2)[N:3]=1.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([NH2:29])=[N:25]1.N1C(C)=CC=CC=1C>O1CCOCC1>[CH:13]1([NH:12][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)[CH:8]=3)[N:3]=[C:2]([NH:29][C:26]3[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=3)[N:11]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 1372541-Methyl-3-aminopyrazoleHCID 86635953HCID 86635953, compound

Product 1

HCID 69016944HCID 69016944, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of [2-Chloro-6-(4-fluoro-phenyl)-quinazolin-4-yl]-cyclopropylamine (150 mg, 0.48 mmol) and 1-Methyl-1H-pyrazol-3-ylamine (70 mg, 0.72 mmol) in 1,4-dioxane (5 ml) was added 2,6-lutidine (2 equiv.; 102 mg, 0.96 mmol). The solution was heated to 100° C. for 3 hours, then cooled and purified by RP HPLC with a gradient of H2O, 0.1% TFA-acetonitrile, to provide the desired product (140 mg, 0.287 mmol, 60% yield). The product was characterized as follows: MS (m/z): 375 ([M+H]+, 100); HPLC Rt=1.60 minutes (Method B).

Workup

  1. temperaturecooled
  2. custompurified by RP HPLC with a gradient of H2O, 0.1% TFA-acetonitrile

Sources & evidence

ORD record
ord-432dda6871c243b5a9313f3249e8ec40
Source dataset
uspto-grants-2016_02
Patent number
US09259426B2

Reaction notes

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