Sodium Bicarbonate → [4-(3-Fluoro-benzyloxy)-phenyl]-(5-methyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-amine

HRID 1829914Notes

Reaction equation

HRID 1829914 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH3:11])[CH:9]=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.Cl.[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=1)[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(#N)C>[F:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=1)[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:2]2[C:7]3=[C:8]([CH3:11])[CH:9]=[CH:10][N:6]3[N:5]=[CH:4][N:3]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 218742274-Chloro-5-methylpyrrolo(2,1-f)(1,2,4)triazineHCID 220552584-(3-Fluoro-benzyloxy)-phenylamine hydrochloride

Product 1

HCID 22055287[4-(3-Fluoro-benzyloxy)-phenyl]-(5-methyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-amineYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-chloro-5-methyl-pyrrolo[2,1-f][1,2,4]triazine (47 mg, 0.281 mmol) (Ref. WO 03/042172 A2) and 4-(3-fluoro-benzyloxy)-phenylamine hydrochloride (70 mg, 0.299 mmol) and NaHCO3 (600 mg, 7.14 mmol) in dry acetonitrile (2 ml) was heated at 80° C. for 8 hr. Filtration followed by removal of the solvent from the filtrate and purification by preparative HPLC afforded the title product (35 mg, 37%) as an oil. Analytical HPLC retention time=1.41 min. (YMC Xterra S7 C18, 3.0×50 mm column, 10–90% aqueous methanol over 2 minutes containing 0.1% TFA, 5 mL/min, monitoring at 220 nm) and a LC/MS M++1=331.

Workup

  1. filtrationFiltration
  2. customfollowed by removal of the solvent from the filtrate and purification by preparative HPLC

Sources & evidence

ORD record
ord-17bf6568219b4b42a2ab63d708ebdc02
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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