Sodium Hydroxide → HCID 20826896, compound

HRID 495491Notes

Reaction equation

HRID 495491 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][O:27][C:28]1[CH:29]=[C:30]([NH2:43])[CH:31]=[CH:32][C:33]=1[O:34][CH2:35][CH:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]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:43][C:30]2[CH:31]=[CH:32][C:33]([O:34][CH2:35][CH:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)=[C:28]([O:27][CH3:26])[CH:29]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 22326811HCID 22326811, compoundHCID 22326883HCID 22326883, compound

Product 1

HCID 20826896HCID 20826896, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °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, 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)-phenylamine (36 mg, 0.14 mmol) in glacial AcOH (2 mL). The reaction, a dark brown solution, was heated to 80° 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 removed in vacuo. The residue was purified by column chromatography (silica; CH2Cl2:MeOH; 9:1, containing TEA [1%]) to afford a brown solid, which was further purified by column chromatography (silica; CH2Cl2:MeOH; 9:1; containing TEA [0.5%]) to afford a light brown solid. MS m/z=564 (M+H). Calc'd for C33H37N7O2=563.

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 removed in vacuo
  6. customThe residue was purified by column chromatography (silica; CH2Cl2:MeOH; 9:1, containing TEA [1%])
  7. customto afford a brown solid, which
  8. customwas further purified by column chromatography (silica; CH2Cl2:MeOH; 9:1; containing TEA [0.5%])
  9. customto afford a light brown solid

Sources & evidence

ORD record
ord-bda8b9891e094446b2be65255218623b
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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