Diisopropylethylamine → HCID 117667157, compound

HRID 1526254Notes

Reaction equation

HRID 1526254 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([CH:30]=1)[O:7][C:8]1[N:9]=[C:10]([NH:21][C:22]2[CH:23]=[N:24][N:25]([CH2:27][CH2:28][OH:29])[CH:26]=2)[C:11]([C:18]([NH2:20])=[O:19])=[N:12][C:13]=1[C:14](O)([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([CH:30]=1)[O:7][C:8]1[N:9]=[C:10]([NH:21][C:22]2[CH:23]=[N:24][N:25]([CH2:27][CH2:28][OH:29])[CH:26]=2)[C:11]([C:18]([NH2:20])=[O:19])=[N:12][C:13]=1[C:14]([CH3:16])=[CH2:15]

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 117666963HCID 117666963, compound

Product 1

HCID 117667157HCID 117667157, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-(5-amino-2-fluorophenoxy)-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (515 mg), diisopropylethylamine (409 μL), and N-methylpyrrolidone (3 mL) was reacted in a microwave reaction device at 200° C. for 4 hours. The mixture was purified by silica gel column chromatography (eluent; chloroform:methanol=98:2-90:10) to obtain 5-(5-amino-2-fluorophenoxy)-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(prop-1-en-2-yl)pyrazine-2-carboxamide (408 mg) as a yellow solid.

Workup

  1. customwas reacted in a microwave reaction device at 200° C. for 4 hours
  2. customThe mixture was purified by silica gel column chromatography (eluent; chloroform:methanol=98:2-90:10)

Sources & evidence

ORD record
ord-707d431d89ff44ea944f568b6705a820
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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