Sodium Hydroxide → HCID 20826899, compound

HRID 495489Notes

Reaction equation

HRID 495489 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]([NH2:46])[CH:31]=[C:32]([O:44][CH3:45])[C:33]=1[O:34][CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]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:46][C:30]2[CH:29]=[C:28]([O:27][CH3:26])[C:33]([O:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]3)=[C:32]([O:44][CH3:45])[CH:31]=2)[N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11844757HCID 11844757, compoundHCID 22326811HCID 22326811, compound

Product 1

HCID 20826899HCID 20826899, 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), 3,5-dimethoxy-4-[2-(4-methylpiperazin-1-yl)-ethoxy]phenylamine (42 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 and 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; 8:2) to afford the title compound as a light purple solid. MS m/z=609 (M+H). Calc'd for C34H40N8O3=608.

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; 8:2)

Sources & evidence

ORD record
ord-8dc7c68eeee54d3ebedb1f87907e0f91
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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