Sodium Carbonate → HCID 178476633, compound

HRID 2056073Notes

Reaction equation

HRID 2056073 reaction equation
C[C:2]1([CH3:27])C(C)(C)OB([C:9]2[CH:26]=[CH:25][C:12]([NH:13][C:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[S:16](=[O:24])(=[O:23])[N:15]=3)=[CH:11][CH:10]=2)[O:3]1.I[C:29]1[C:37]2[C:32](=[N:33][CH:34]=[N:35][C:36]=2[NH2:38])[N:31]([C@H:39]2[CH2:44][CH2:43][C@H:42]([N:45]3[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]3)[CH2:41][CH2:40]2)[N:30]=1.C(=O)([O-])[O-:53].[Na+].[Na+]>COCCOC.O>[C:2]([OH:53])(=[O:3])[CH3:27].[NH2:38][C:36]1[N:35]=[CH:34][N:33]=[C:32]2[N:31]([C@H:39]3[CH2:44][CH2:43][C@H:42]([N:45]4[CH2:46][CH2:47][N:48]([CH3:51])[CH2:49][CH2:50]4)[CH2:41][CH2:40]3)[N:30]=[C:29]([C:9]3[CH:10]=[CH:11][C:12]([NH:13][C:14]4[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[S:16](=[O:23])(=[O:24])[N:15]=4)=[CH:25][CH:26]=3)[C:37]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 69204388HCID 69204388, compoundHCID 178481015HCID 178481015, compound

Product 1

HCID 178476633HCID 178476633, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilino]-1H-1λ6-benzo[d]isothiazole-1,1-dione (0.09 g, 0.000234 mol), trans-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.08 g, 0.00018 mol), tetrakis-(triphenylphosphine)palladium (0.013 g, 0.000011 mol) and sodium carbonate (0.048 g, 0.00045 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; 10-60% 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}anilino)-1H-1λ6-benzo[d]isothiazole-1,1-dione acetate (0.075 g, 0.000119 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-7af2af539398473c8847abe17842d2be
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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