Sodium Hydroxide → HCID 20826897, compound

HRID 495492Notes

Reaction equation

HRID 495492 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([C:18]2[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=2[CH3:25])[C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.[OH-].[Na+]>CC(O)=O>[NH:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[N:8]([C:18]1[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:25])[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:39][C:36]2[CH:35]=[CH:34][C:33]([N:30]3[CH2:29][CH2:28][N:27]([CH3:26])[CH2:32][CH2:31]3)=[CH:38][CH:37]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 22326811HCID 22326811, compound

Product 1

HCID 20826897HCID 20826897, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A pressure tube was charged with a solution of 2-(N-(2-chloropyrimid-4-yl)-2,6-dimethylphenylamino)-1H-benzimidazole (50 mg, 0.14 mmol), from Example 155 Step F, 4-(4-methylpiperazin-1-yl)-phenylamine (27 mg, 0.14 mmol) in glacial AcOH (2 mL). The reaction, a dark brown solution, was heated to 100° C. for 18 h. The reaction was cooled to RT then basified by careful addition of 5M NaOH (15 mL). The aqueous solution was extracted with CH2Cl2. The combined organic extracts were dried (Na2SO4) and the solvent was removed in vacuo. The residue was purified by column chromatography (silica; CH2Cl2:MeOH; 9:1; containing TEA (0.2%)) to afford a light brown solid. MS m/z=505 (M+H). Calc'd for C30H32N8=504.

Workup

  1. customThe reaction
  2. temperatureThe reaction was cooled to RT
  3. extractionThe aqueous solution was extracted with CH2Cl2
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by column chromatography (silica; CH2Cl2:MeOH; 9:1; containing TEA (0.2%))
  7. customto afford a light brown solid

Sources & evidence

ORD record
ord-e0fa3897e52c4b6f925fb39e3ea6c91b
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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