Trimethyl orthoformate → HCID 67261289, compound

HRID 79326Notes

Reaction equation

HRID 79326 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]([NH:26][NH2:27])=[O:25])=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=2)[N:4]=1)[CH3:2].[CH3:36]OC(OC)OC>>[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[O:25][CH:36]=[N:27][N:26]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[N:30]=2)[N:4]=1)[CH3:2]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 67261308N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(hydrazinecarbonyl)imidazo[1,2-a]pyridine-3-carboxamide

Product 1

HCID 67261289HCID 67261289, compoundYield 32.7%

Conditions

Temperature
110 °C

Procedure

To N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(hydrazinecarbonyl)imidazo[1,2-a]pyridine-3-carboxamide (15 mg, 0.0320 mmol) was added trimethoxymethane (340 mg, 3.20 mmol). The reaction mixture was sealed and heated to 110° C. for 30 minutes. The mixture was cooled to ambient temperature and concentrated under reduced pressure. Silica gel chromatography (DCM/MeOH 10:1) gave the final product (5 mg). MS (ES+APCI) m/z=479 (M+H).

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe mixture was cooled to ambient temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d832f66eb6b748f6aa0f02e2c84f1e6e
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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