Acetic Acid → HCID 58588036, compound

HRID 446347Notes

Reaction equation

HRID 446347 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:11]([CH3:30])[CH:10]=1)=[O:7])=O.[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH2:38].CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:34][N:35]([CH3:39])[CH2:36][CH2:37][NH:38][CH2:1][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][CH:33]=1)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH3:29])[N:23]=3)=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:11]([CH3:30])[CH:10]=1)=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 66053N,N-DimethylethylenediamineHCID 5049666Sodium triacetoxyborohydrideHCID 58588081HCID 58588081, compound

Product 1

HCID 58588036HCID 58588036, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-formyl-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide (0.100 g, 0.23 mmol) in MeOH (6 mL) was added N1,N1-dimethylethane-1,2-diamine (0.13 mL, 1.1 mmol) and AcOH (0.010 mL, 0.23 mmol). The reaction was allowed to stir for 2.5 h, at which point sodium triacetoxyborohydride (0.096 g, 0.46 mmol) was added. After approximately 16 h, the reaction was quenched by the addition of saturated aqueous sodium bicarbonate. The aqueous layer was extracted four times with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a solid. Purification by reverse-phase HPLC using acetonitrile/water/TFA as eluent gave 3-((2-(dimethylamino)ethylamino)methyl)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide as a white solid. MS m/z=512 [M+1]+. Calc'd for C29H33N7O2: 511.63.

Workup

  1. additionwas added
  2. customthe reaction was quenched by the addition of saturated aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted four times with dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a solid
  8. customPurification by reverse-phase

Sources & evidence

ORD record
ord-c5ac6e3e9c214277b8d93d13ebda9a78
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

Loading…