Acetic Acid → HCID 58588036, compound

HRID 1361704Notes

Reaction equation

HRID 1361704 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-ac691bb9b80d4d659bee4e6e4779cd1e
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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