Methanol → HCID 21081720, compound

HRID 2117066Notes

Reaction equation

HRID 2117066 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:19])[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CO.[NH4+].[Cl-]>C1COCC1.[Zn]>[NH2:24][C:22]1[CH:21]=[CH:20][C:3]([O:4][C:5]2[C:10]3=[C:11]([CH3:19])[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:13][N:9]3[N:8]=[CH:7][N:6]=2)=[C:2]([F:1])[CH:23]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 21081719HCID 21081719, compound

Product 1

HCID 21081720HCID 21081720, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (36 mg, 0.1 mmol) in THF (1.0 mL) was added MeOH (0.7 mL) followed by Zn (130 mg, 2.0 mmol) and NH4Cl (53 mg, 1.0 mmol). The reaction was heated at 70° C. overnight. LC/MS analysis indicated mostly starting material. The solution was shaken vigorously and then heated to 75° C. LC/MS analysis after 4 h showed the desired product and many other peaks. The reaction was filtered through a coarse filter, and the filtrate was concentrated to a give 55 mg of a brown residue. The residue was suspended in THF and passed through an HPLC filter resulting in a clear filtrate. The filtrate was concentrated in vacuo to give 54 mg of the title compound as a crude mixture which was used in the next step without further purification.

Workup

  1. temperatureheated to 75° C

Sources & evidence

ORD record
ord-a78a0c9e440243178fe429f558850658
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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