Piperazine → HCID 57813467, compound

HRID 564577Notes

Reaction equation

HRID 564577 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:48][CH3:49])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]=O)[CH:41]=5)[C:36]([CH3:39])=[CH:37][CH:38]=4)=[O:30])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[NH:50]1[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:48][CH3:49])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[C:35]([C:40]5[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][N:50]6[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]6)[CH:41]=5)[C:36]([CH3:39])=[CH:37][CH:38]=4)=[O:30])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 4837PiperazineHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 57813304HCID 57813304, compound

Product 1

HCID 57813467HCID 57813467, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N′-[(3′-formyl-6-methyl-3-biphenylyl)methyl]-1,3-benzenedicarboxamide (0.033 g, 0.05 mmol), and piperazine (0.043 g, 0.5 mmol) were combined in CH2Cl2 (2 mL) and stirred for 30 min. Sodium triacetoxyborohydride (0.0318 g, 0.15 mmol) was added and the mixture stirred for 30 h. Aqueous workup was followed using a Gilson HPLC with a TFA system. The purified compound was taken up in EtOAc, washed 3× with 1 N NaOH, 1× with brine, dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound as a white solid. LC-MS m/z 729.4 (M+H)+, 1.31 min (ret time); mp 135-138° C. Analytical HPLC shows 98.4% purity, (ret time 10.019 min).

Workup

  1. stirringthe mixture stirred for 30 h
  2. washwashed 3× with 1 N NaOH, 1× with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ceb757750b74e8c9b70445fbf63cf2a
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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