Sodium Carbonate → HCID 117667470, compound

HRID 1526209Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([N:26]4[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[C:16]([CH3:33])[CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].CC1(C)C(C)(C)OB([C:42]2[CH:43]=[C:44]([CH:46]=[CH:47][CH:48]=2)[NH2:45])O1.CN1CCCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:45][C:44]1[CH:43]=[C:42]([C:2]2[N:3]=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:21][CH2:22][CH:23]([N:26]5[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]5)[CH2:24][CH2:25]4)=[C:16]([CH3:33])[CH:15]=3)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=2[CH2:8][CH3:9])[CH:48]=[CH:47][CH:46]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, to a mixture of 5-chloro-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (200 mg), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (93 mg), and N-methylpyrrolidone (2 mL) were added tetrakistriphenylphosphine palladium (0) (25 mg) and a 2 M aqueous sodium carbonate solution (424 μL), followed by stirring in a microwave reaction device at 100° C. for 1 hour. Water was added thereto, and the solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1) to obtain 5-(3-aminophenyl)-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (125 mg) as an orange solid.

Workup

filtrationthe solid was collected by filtration
customThe obtained solid was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-100:10:1)

Sources & evidence

ORD record: ord-5ac53f5e087145888ef513500492720d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085540B2

Reaction notes

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