Diisopropyl Ether → tert-butyl (R)-3-((5-carbamoyl-3-ethyl-6-((4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrazin-2-yl)oxy)pyrrolidine-1-carboxylate

HRID 1526190Notes

Reaction equation

HRID 1526190 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:24][CH3:25])[C:7]([O:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:8][C:9]=1Cl)(=[O:3])[NH2:2].[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([CH:33]2[CH2:38][CH2:37][N:36]([C:39]3[CH:45]=[CH:44][C:42]([NH2:43])=[CH:41][CH:40]=3)[CH2:35][CH2:34]2)[CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C.C(OC(C)C)(C)C>O.CN1CCCC1=O>[C:1]([C:4]1[N:5]=[C:6]([CH2:24][CH3:25])[C:7]([O:11][C@@H:12]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)=[N:8][C:9]=1[NH:43][C:42]1[CH:44]=[CH:45][C:39]([N:36]2[CH2:37][CH2:38][CH:33]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)[CH2:34][CH2:35]2)=[CH:40][CH:41]=1)(=[O:3])[NH2:2]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 81531DiisopropylethylamineHCID 580157484-(4-(4-Methyl-1-piperazinyl)-1-piperidinyl)benzenamineHCID 117675595Tert-butyl (R)-3-((5-carbamoyl-6-chloro-3-ethylpyrazin-2-YL)oxy)pyrrolidine-1-carboxylate

Product 1

HCID 117675491tert-butyl (R)-3-((5-carbamoyl-3-ethyl-6-((4-(4-(4-methylpiperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrazin-2-yl)oxy)pyrrolidine-1-carboxylateYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of tert-butyl (3R)-3-[(5-carbamoyl-6-chloro-3-ethylpyrazin-2-yl)oxy]pyrrolidine-1-carboxylate (90 mg), 4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]aniline (210 mg), diisopropylethylamine (140 μL), and N-methylpyrrolidone (500 μL) was reacted using a microwave reaction device at 150° C. for 2 hours. The reaction mixture was left to be cooled, and then water and diisopropyl ether were added thereto. The insoluble matter was collected by filtration to obtain tert-butyl (3R)-3-{[5-carbamoyl-3-ethyl-6-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazin-2-yl]oxy}pyrrolidine-1-carboxylate (101 mg) as a yellowish brown solid.

Workup

  1. customwas reacted
  2. customa microwave reaction device at 150° C. for 2 hours
  3. waitThe reaction mixture was left
  4. temperatureto be cooled
  5. filtrationThe insoluble matter was collected by filtration

Sources & evidence

ORD record
ord-38e86a4c45e64e1b8ae54457cdbf41f1
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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