Sodium Carbonate → HCID 178476632, compound

HRID 898009Notes

Reaction equation

HRID 898009 reaction equation
C[C:2]1([CH3:29])C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:19]=4[O:18][N:17]=3)=[CH:11][CH:10]=2)[O:3]1.I[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[N:37][C:38]=2[NH2:40])[N:33]([C@H:41]2[CH2:46][CH2:45][C@H:44]([N:47]3[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]3)[CH2:43][CH2:42]2)[N:32]=1.C(=O)([O-])[O-:55].[Na+].[Na+]>COCCOC.O>[C:2]([OH:55])(=[O:3])[CH3:29].[NH2:40][C:38]1[N:37]=[CH:36][N:35]=[C:34]2[N:33]([C@H:41]3[CH2:46][CH2:45][C@H:44]([N:47]4[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]4)[CH2:43][CH2:42]3)[N:32]=[C:31]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]4[C:20]5[CH:21]=[CH:22][C:23]([C:25]([F:27])([F:28])[F:26])=[CH:24][C:19]=5[O:18][N:17]=4)=[CH:13][CH:14]=3)[C:39]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 22347246HCID 22347246, compoundHCID 178481015HCID 178481015, compound

Product 1

HCID 178476632HCID 178476632, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-N-[6-(trifluoromethyl)benzo[d]isoxazol-3-yl]amine (0.062 g, 0.000153 mol), trans-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.065 g, 0.000146 mol), tetrakis-(triphenylphosphine)palladium (0.010 g, 0.0000087 mol) and sodium carbonate (0.039 g, 0.000365 mol) was heated in a mixture of ethylene glycol dimethyl ether (4 mL) and water (2 mL) at 80° C. for 16 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; 10-70% acetonitrile-0.1M ammonium acetate over 30 min, 21 mL/min) to yield trans-N3-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-6-(trifluoromethyl)benzo[d]isoxazol-3-amine acetate (0.026 g, 0.0000398 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; 10-70% acetonitrile-0.1M ammonium acetate over 30 min, 21 mL/min)

Sources & evidence

ORD record
ord-0ee9a9a079e44706889ffd1057c2321f
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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