Diisopropylethylamine → HCID 117666881, compound

HRID 1526225Notes

Reaction equation

HRID 1526225 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)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[NH2:33][CH2:34][CH:35]1[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]1.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[C:10]([C:5]1[N:6]=[C:7]([CH2:8][CH3:9])[C:2]([NH:33][CH2:34][CH:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]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)=[CH:16][CH:15]=1)(=[O:11])[NH2:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 885697085-Chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide

Product 1

HCID 117666881HCID 117666881, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-chloro-6-ethyl-3-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazine-2-carboxamide (200 mg), tert-butyl 4-(aminomethyl)piperidine-1-carboxylate (300 μL), diisopropylethylamine (240 μL), and N-methylpyrrolidone (0.8 mL) was reacted in a microwave reaction device at 160° C. for 2 hours. The mixture was subjected to liquid separation with ethyl acetate and water, and the organic phase was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was washed with diisopropyl ether to obtain tert-butyl 4-({[5-carbamoyl-3-ethyl-6-({4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl}amino)pyrazin-2-yl]amino}methyl)piperidine-1-carboxylate (195 mg) as a pale yellow solid.

Workup

  1. customwas reacted in a microwave reaction device at 160° C. for 2 hours
  2. customThe mixture was subjected to liquid separation with ethyl acetate and water
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe obtained residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-75ece3596624462da1f881e24ca04679
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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