Potassium Carbonate → HCID 117667076, compound

HRID 1526226Notes

Reaction equation

HRID 1526226 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].[NH2:34][CH2:35][CH:36]1[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:37]1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O.C(OCC)(=O)C>[C:10]([C:5]1[N:6]=[C:7]([CH2:8][CH3:9])[C:2]([NH:34][CH2:35][CH:36]2[CH2:39][N:38]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:37]2)=[N:3][C:4]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][CH:23]([N:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)[CH2:22][CH2:21]2)=[C:16]([CH3:33])[CH:15]=1)(=[O:11])[NH2:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylateHCID 88569548HCID 88569548, compound

Product 1

HCID 117667076HCID 117667076, compoundYield 27.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-chloro-6-ethyl-3-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (350 mg), tert-butyl 3-(aminomethyl)azetidine-1-carboxylate (266 mg), potassium carbonate (154 mg), and N-methylpyrrolidone (7 mL) was reacted at 100° C. for 11.5 hours. To the mixture were added ethyl acetate and water, followed by liquid separation. The organic phase was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1) to obtain tert-butyl 3-({[5-carbamoyl-3-ethyl-6-({3-methyl-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazin-2-yl]amino}methyl)azetidine-1-carboxylate (128 mg) as a yellow solid.

Workup

  1. customwas reacted at 100° C. for 11.5 hours
  2. customfollowed by liquid separation
  3. washThe organic phase was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1)

Sources & evidence

ORD record
ord-bfa7ce5a5b2a4a8b8b117e4f96db250c
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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