Ethyl formate → HCID 58010272, compound

HRID 1854466Notes

Reaction equation

HRID 1854466 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.[CH:32](OCC)=[O:33]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][CH:32]=[O:33])[N:20]=[C:15]2[CH:14]=1

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 58009787HCID 58009787, compound

Product 1

HCID 58010272HCID 58010272, compoundYield 100%

Procedure

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.095 g, 0.22 mmol, Example #20, Step G) in ethyl formate (4.4 mL, 54.0 mmol) was heated at about 60° C. in an oil bath for about 45 min. The mixture was cooled and evaporated to give N-((6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)formamide (0.10 g, 100%): LC/MS (Table 2, Method a) Rt=2.65 min; MS m/z: 466 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. customevaporated

Sources & evidence

ORD record
ord-5f8d70faafbf4b3eb32b2a52b07af516
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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