Ammonium Hydroxide → HCID 57813514, compound

HRID 564578Notes

Reaction equation

HRID 564578 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](C=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].[CH3:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1.[C:57](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[NH4+]>C(Cl)Cl>[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]([CH2:50][N:51]6[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]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[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 57813304HCID 57813304, compound

Product 1

HCID 57813514HCID 57813514, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 1-methylpiperazine (0.025 g, 0.25 mmol) were combined in CH2Cl2 (2 mL) and stirred for 30 min. Sodium triacetoxyborohydride (0.053 g, 0.25 mmol) was added and the mixture stirred overnight. Aqueous workup followed using a Gilson HPLC with an ammonium hydroxide system gave the title compound as a white solid. LC-MS m/z 743.2 (M+H)+, 1.42 min (ret time); mp 121-124° C.

Workup

  1. stirringthe mixture stirred overnight

Sources & evidence

ORD record
ord-7969b822c4254283ad6a20ed14458387
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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