Water → 6-{1-[2-(4-Bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl]cyclopropyl}quinoline

HRID 500213Notes

Reaction equation

HRID 500213 reaction equation
[Br: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][C:3]=1[F:15].Cl[CH:17]([C:20]1([C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[N:29]=[CH:28][CH:27]=[CH:26]3)[CH2:22][CH2:21]1)[CH:18]=O.O.C(N(CC)CC)C>C(O)(C)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]3[N:12]([C:17]([C:20]4([C:23]5[CH:24]=[C:25]6[C:30](=[CH:31][CH:32]=5)[N:29]=[CH:28][CH:27]=[CH:26]6)[CH2:22][CH2:21]4)=[CH:18][N:14]=3)[N:13]=2)=[CH:4][C:3]=1[F:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 575165236-(4-Bromo-3-fluorophenyl)-1,2,4-triazin-3-amineHCID 86621504Chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde

Product 1

HCID 672239136-{1-[2-(4-Bromo-3-fluorophenyl)imidazo[1,2-b][1,2,4]triazin-7-yl]cyclopropyl}quinoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-(4-bromo-3-fluorophenyl)-1,2,4-triazin-3-amine (80.0 mg, 0.297 mmol, Example 7, Steps 1-5) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.088 g, 0.36 mmol) in isopropyl alcohol (3 mL) and a drop of water was heated at 110° C. for 48 h. The mixture was adjusted to pH 9 with triethylamine. The volatiles were removed under reduced pressure. The residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-60%) to afford the desired product. LCMS: (M+H)=459.9/461.9.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customThe residue was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-60%)

Sources & evidence

ORD record
ord-e48ba32543f34dad93b5630023a9050d
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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