Diisopropylethylamine → HCID 117675777, compound

HRID 1526252Notes

Reaction equation

HRID 1526252 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:15][C:16]2[CH:17]=[N:18][N:19]([CH2:21][CH2:22][OH:23])[CH:20]=2)[C:5]([C:12]([NH2:14])=[O:13])=[N:6][C:7]=1[C:8](O)([CH3:10])[CH3:9].[NH2:24][C@@H:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]1.C(N(C(C)C)CC)(C)C.[Cl-].[Na+].O.O>CN1CCCC1=O>[C:12]([C:5]1[N:6]=[C:7]([C:8]([CH3:10])=[CH2:9])[C:2]([NH:24][C@@H:25]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]2)=[N:3][C:4]=1[NH:15][C:16]1[CH:17]=[N:18][N:19]([CH2:21][CH2:22][OH:23])[CH:20]=1)(=[O:13])[NH2:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 23713072Sodium chloride dihydrateHCID 117667243HCID 117667243, compound

Product 1

HCID 117675777HCID 117675777, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-chloro-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (700 mg), tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate (1.05 mL), diisopropylethylamine (1.06 mL), and N-methylpyrrolidone (2.5 mL) was reacted in a microwave reaction device at 180° C. for 1 hour. To the reactant was added a mixed solution of saturated brine:water (1:1), followed by extraction with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10, NH2 type: eluent; chloroform:methanol=99:1-95:5) to obtain tert-butyl (3R)-3-{[5-carbamoyl-6-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-3-(prop-1-en-2-yl)pyrazin-2-yl]amino}pyrrolidine-1-carboxylate (928 mg) as a yellow amorphous substance.

Workup

  1. customwas reacted in a microwave reaction device at 180° C. for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10, NH2 type: eluent; chloroform:methanol=99:1-95:5)

Sources & evidence

ORD record
ord-d747252ace1e4fa1860dab99af807d8c
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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