6-(4-Fluorophenyl)-1,2,4-triazin-3-amine → 2-(4-Fluorophenyl)-7-[1-(4-methoxyphenyl)cyclopropyl]imidazo[1,2-b]-[1,2,4]-triazine

HRID 500111Notes

Reaction equation

HRID 500111 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[N:12][C:11]([NH2:14])=[N:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[CH:16]([C:19]1([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:21][CH2:20]1)[CH:17]=O>C(O)(C)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:16]([C:19]4([C:22]5[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=5)[CH2:20][CH2:21]4)=[CH:17][N:14]=3)[N:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 672240676-(4-Fluorophenyl)-1,2,4-triazin-3-amineHCID 86621500Chloro[1-(4-methoxyphenyl)cyclopropyl]acetaldehyde

Product 1

HCID 251455102-(4-Fluorophenyl)-7-[1-(4-methoxyphenyl)cyclopropyl]imidazo[1,2-b]-[1,2,4]-triazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-(4-fluorophenyl)-1,2,4-triazin-3-amine (20.1 mg, 0.106 mmol) and chloro[1-(4-methoxyphenyl)cyclopropyl]acetaldehyde (53 mg, 0.24 mmol) in isopropyl alcohol (0.6 mL) was heated to 90° C. overnight. After cooling, the mixture was diluted with methanol and was purified by mass-guided RP-HPLC to afford the desired product. LCMS: (M+H)=361.1.

Workup

  1. temperatureAfter cooling
  2. customwas purified by mass-guided RP-HPLC

Sources & evidence

ORD record
ord-757814f36067445eb5f81669db0c49bb
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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