Sodium Carbonate Monohydrate → HCID 178476555, compound

HRID 432340Notes

Reaction equation

HRID 432340 reaction equation
[CH2:1]([CH:8]1[O:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17](B3[O:24][C:23]([CH3:26])(C)C(C)(C)O3)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:30]1[C:38]2[C:33](=[N:34][CH:35]=[N:36][C:37]=2[NH2:39])[N:32]([C@H:40]2[CH2:45][CH2:44][C@H:43]([N:46]3[CH2:51][CH2:50][N:49]([CH3:52])[CH2:48][CH2:47]3)[CH2:42][CH2:41]2)[N:31]=1.[OH2:53].C(=O)([O-])[O-:55].[Na+].[Na+]>COCCOC.O>[C:23]([OH:55])(=[O:24])[CH3:26].[C:8]([OH:12])(=[O:53])[CH3:1].[NH2:39][C:37]1[N:36]=[CH:35][N:34]=[C:33]2[N:32]([C@H:40]3[CH2:45][CH2:44][C@H:43]([N:46]4[CH2:47][CH2:48][N:49]([CH3:52])[CH2:50][CH2:51]4)[CH2:42][CH2:41]3)[N:31]=[C:30]([C:17]3[CH:16]=[CH:15][C:14]([N:10]4[CH2:9][CH:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[O:12][C:11]4=[O:13])=[CH:19][CH:18]=3)[C:38]=12

Participants

6

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 223471605-Benzyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-oxazolan-2-oneHCID 178481015HCID 178481015, compound

Product 1

HCID 178476555HCID 178476555, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-benzyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-oxazolan-2-one (0.110 g, 0.00029 mol), trans-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.080 g, 0.000181 mol), tetrakis-(triphenylphosphine)palladium (0.012 g, 0.000011 mol) and sodium carbonate monohydrate (0.056 g, 0.00045 mol) was heated in a mixture of ethylene glycol dimethyl ether (5 mL) and water (3 mL) at 80° C. for sixteen hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield trans-3-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-benzyl-1,3-oxazolan-2-one diacetate (0.049 g, 0.000072 mol) as a white solid.

Workup

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-f50d63e8575a445e8eed4c0b0d9b19ae
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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