4-Pyridinecarboxaldehyde → HCID 60204334, compound

HRID 2267313Notes

Reaction equation

HRID 2267313 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH2:17][CH2:18][N:19]4[C:23]([CH3:25])([CH3:24])[C:22](=[O:26])[NH:21][C:20]4=[O:27])[N:11]=3)=[CH:7][C:6]=2[CH:28]=1.[CH:29](=O)[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:24][C:23]1([CH3:25])[N:19]([CH2:18][CH2:17][NH:16][C:12]2[N:11]=[C:10]([C:8]3[S:9][C:5]4[CH:4]=[CH:3][C:2]([NH:1][CH2:29][C:30]5[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=5)=[CH:28][C:6]=4[CH:7]=3)[CH:15]=[CH:14][N:13]=2)[C:20](=[O:27])[NH:21][C:22]1=[O:26]

Participants

7

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 60204330HCID 60204330, compound

Product 1

HCID 60204334HCID 60204334, compoundYield 27.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

1-(2-(4-(5-aminobenzothiophen-2-yl)pyrimidin-2-ylamino)ethyl)-5,5-dimethyl imidazo-lidin-2,4-dione (300 mg, 0.758 mmol) was suspended in dichloromethane (10 mL). Isonicotinaldehyde (97.4 mg, 0.910 mmol), acetic acid (4-5 drops), and sodium triacetoxy-borohydride (321 mg, 1.516 mmol) were added, and the mixture was heated to 60° C. for 16 h. The reaction was cooled to room temperature, diluted with a saturated aqueous solution of sodium bicarbonate (15 mL), and extracted with dichloromethane (4×15 mL). The organic layers were combined and then washed in turn with a saturated aqueous solution of sodium bicarbonate (10 mL), deionized water (15 mL), and a saturated aqueous solution of sodium chloride (15 mL). The organic layer was separated, dried over sodium sulfate (200 mg), filtered through a coarse frit (to remove the sodium sulfate), and concentrated in vacuo to give a white solid (100 mg). The crude material was purified by flash chromatography (MeOH/DCM) to yield the title compound as a white powder (20 mg). MS (M+H)+ 488.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with dichloromethane (4×15 mL)
  3. washwashed in turn with a saturated aqueous solution of sodium bicarbonate (10 mL), deionized water (15 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate (200 mg)
  6. filtrationfiltered through a coarse frit (
  7. customto remove the sodium sulfate), and
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27b41409fcba46c59f75e56d0c768c71
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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