1,2-Dimethoxyethane → HCID 178488189, compound

HRID 2056149Notes

Reaction equation

HRID 2056149 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:3]=1.C[C:26]1([CH3:49])C(C)(C)OB([C:33]2[CH:48]=[CH:47][C:36]([CH2:37][N:38]3[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=4[N:40]=[CH:39]3)=[CH:35][CH:34]=2)[O:27]1.C(=O)([O-])[O-:51].[Na+].[Na+].[CH3:56][O:57]CCOC>O>[C:26]([OH:51])(=[O:27])[CH3:49].[NH3:3].[N:38]1([CH2:37][C:36]2[CH:35]=[CH:34][C:33]([C:2]3[C:10]4[C:5](=[N:6][CH:7]=[N:8][C:9]=4[NH2:11])[N:4]([C@H:12]4[CH2:17][CH2:16][C@H:15]([N:18]5[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]5)[CH2:14][CH2:13]4)[N:3]=3)=[CH:48][C:47]=2[O:57][CH3:56])[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:40]=[CH:39]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 22347008HCID 22347008, compoundHCID 178481015HCID 178481015, compound

Product 2

HCID 12432Ammonia acetateHCID 178488189HCID 178488189, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

trans-3-Iodo-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.453 mmol), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]-1H-benzo[d]imidazole (303 mg, 0.906 mmol), palladium tetrakistriphenyphosphine (0.31 mg, 0.027 mmol) and sodium carbonate (155 mg, 1.09 mmol) were mixed with ethylene glycol dimethyl ether (5 mL) and water (2.5 mL). The reaction mixture was heated at reflux overnight under nitrogen. The solvent was removed and the residue was purified by reverse phase preparative HPLC (Rainin HPLC, Column: Thermoquest, hyperprep HS C18, 8 um, 250×21.2 mm. Eluents: 5% B/A to 100% B/A in 25 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 21 mL/min.) to give trans-3-[4-(1H-benzo[d]imidazol-1-ylmethyl)-3-methoxyphenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (35 mg, 15%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight under nitrogen
  3. customThe solvent was removed
  4. customthe residue was purified by reverse phase preparative HPLC (Rainin HPLC, Column

Sources & evidence

ORD record
ord-13ba731ff5ee471a832c9dd20b0d6bc4
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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