Potassium Carbonate → HCID 59427332, compound

HRID 1042837Notes

Reaction equation

HRID 1042837 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]([C:31]5[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](CC)(CC)CC)=[CH:33][CH:32]=5)=[N:23][N:22]=4)=[CH:16][CH:15]=3)=[CH:8][CH:9]=[N:10]2)=[N:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([NH:20][C:17]3[CH:16]=[CH:15][C:14]([O:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][N:5]=5)[N:10]=[CH:9][CH:8]=4)=[CH:19][CH:18]=3)=[N:22][N:23]=2)=[CH:32][CH:33]=1)#[CH:38]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67316053N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-(2-(triethylsilyl)ethynyl)phenyl)phthalazin-1-amine

Product 1

HCID 59427332HCID 59427332, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

In a nitrogen purged sealed tube was dissolved N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)-4-(4-(2-(triethylsilyl)ethynyl)phenyl)phthalazin-1-amine (0.100 g, 0.164 mmol) in MeOH (2.00 mL). Potassium carbonate (0.068 g, 0.492 mmol) was added and the reaction was stirred at 20° C. for 24 h and then concentrated. The crude was extracted into DCM, washed 1× with water, 1× with brine, dried over Na2SO4, filtered through flitted funnel, concentrated. The resulting crude material was purified by silica gel chromatography eluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2. The product fractions were concentrated to afford 4-(4-ethynylphenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine as light yellow solid. MS [M+H]=496; Calc'd 495.5 for C31H21N5O2.

Workup

  1. customIn a nitrogen purged
  2. customsealed tube
  3. concentrationconcentrated
  4. extractionThe crude was extracted into DCM
  5. washwashed 1× with water, 1× with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered through flitted funnel
  8. concentrationconcentrated
  9. customThe resulting crude material was purified by silica gel chromatography
  10. washeluting with 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2
  11. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-bda7890a54a7481392fb3d5be81abaf6
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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