1-Ethylpiperazine → HCID 57813531, compound

HRID 564579Notes

Reaction equation

HRID 564579 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([CH2:16][NH:17][C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([NH:28][CH2:29][C:30]4[C:31]([NH:43][CH:44]5[CH2:49][CH2:48][O:47][CH2:46][CH2:45]5)=[C:32]5[CH:40]=[N:39][N:38]([CH2:41][CH3:42])[C:33]5=[N:34][C:35]=4[CH2:36][CH3:37])=[O:27])[CH:21]=3)=[O:19])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH2:50]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)[CH3:51]>C1COCC1>[CH2:41]([N:38]1[C:33]2=[N:34][C:35]([CH2:36][CH3:37])=[C:30]([CH2:29][NH:28][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([C:18]([NH:17][CH2:16][C:11]4[CH:10]=[C:9]([C:5]5[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][N:55]6[CH2:56][CH2:57][N:52]([CH2:50][CH3:51])[CH2:53][CH2:54]6)[CH:4]=5)[C:14]([F:15])=[CH:13][CH:12]=4)=[O:19])[CH:21]=3)=[O:27])[C:31]([NH:43][CH:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[C:32]2[CH:40]=[N:39]1)[CH3:42]

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 57813319HCID 57813319, compound

Product 1

HCID 57813531HCID 57813531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-{[3′-(Chloromethyl)-6-fluoro-3-biphenylyl]methyl}-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide (0.034 g, 0.05 mmol) and 1-ethylpiperazine (0.0285 g, 0.25 mmol) were combined in THF (1 mL) and microwaved at 150° C. for 1 h. The mixture was purified using a Gilson HPLC with a TFA system followed by passing the product though a quaternary ammonium hydroxide cartridge to give the free base, the title compound, as a tan solid. LC-MS m/z 760.8 (M+H)+, 1.55 min (ret time); mp 155-158° C. Analytical HPLC shows 95.7% purity, (ret time 10.098 min).

Workup

  1. custommicrowaved at 150° C. for 1 h
  2. customThe mixture was purified
  3. customto give the free base

Sources & evidence

ORD record
ord-54613e3351a14641a14197f06ab020d8
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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