HCID 117667517, compound → HCID 117666846, compound

HRID 1526243Notes

Reaction equation

HRID 1526243 reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH2:10][O:11][C:12]1[N:13]=[C:14]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH2:35][CH2:34][CH:33]([N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]4)[CH2:32][CH2:31]3)=[CH:26][CH:25]=2)[C:15]([C:20]([NH2:22])=[O:21])=[N:16][C:17]=1[CH2:18][CH3:19])C1C=CC=CC=1>[Pd].C(O)(=O)C>[NH2:8][CH2:9][CH2:10][O:11][C:12]1[N:13]=[C:14]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([N:30]3[CH2:31][CH2:32][CH:33]([N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]4)[CH2:34][CH2:35]3)=[CH:28][CH:29]=2)[C:15]([C:20]([NH2:22])=[O:21])=[N:16][C:17]=1[CH2:18][CH3:19]

Participants

4

Reactant 1

HCID 117667517HCID 117667517, compound

Product 1

HCID 117666846HCID 117666846, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a mixture of 5-[2-(dibenzylamino)ethoxy]-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (172 mg) and acetic acid (2.84 mL) was added 10% palladium-supported carbon (53% wet product) (55 mg), followed by stirring at room temperature for 6 hours under a hydrogen gas atmosphere (4 atm). The mixture was filtered through celite, and then 20% palladium hydroxide-supported carbon (36 mg) was added thereto, followed by stirring overnight under a hydrogen gas atmosphere (4 atm). The mixture was filtered through celite and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=99:1) to obtain 5-(2-aminoethoxy)-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (123 mg) as a yellow solid.

Workup

  1. filtrationThe mixture was filtered through celite
  2. addition20% palladium hydroxide-supported carbon (36 mg) was added
  3. stirringby stirring overnight under a hydrogen gas atmosphere (4 atm)
  4. filtrationThe mixture was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH2 type: eluent; chloroform:methanol=99:1)

Sources & evidence

ORD record
ord-db2551f943e14874b6ef5bcc344aaaf7
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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