Propanal → HCID 44610256, compound

HRID 1398012Notes

Reaction equation

HRID 1398012 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:9]=2/[CH:10]=[C:11]2/[C:12](=[O:17])[NH:13][C:14](=[O:16])[S:15]/2)[CH2:3]1.[CH:23](=O)[CH2:24][CH3:25].C(O[BH-](O[C:37](=O)[CH3:38])OC(=O)C)(=O)C.[Na+].[C:41]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:22][C:21]1[C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C@@H:2]([N:1]([CH2:41][CH2:37][CH3:38])[CH2:23][CH2:24][CH3:25])[CH2:3]2)=[C:9]([CH:18]=[CH:19][CH:20]=1)/[CH:10]=[C:11]1/[C:12](=[O:17])[NH:13][C:14](=[O:16])[S:15]/1

Participants

6

Reactant 4

HCID 527PropanalHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 44609163HCID 44609163, compound

Product 1

HCID 44610256HCID 44610256, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (R,Z)-5-(2-(3-aminopiperidin-1-yl)-3-chlorobenzylidene)thiazolidine-2,4-dione (122D) (100 mg, 0.27 mmol) and propionaldehyde (20.17 mg, 0.35 mmol) in CH2Cl2 (15 mL) was stirred at 50° C. for 20 min. before sodium triacetoxyborohydride (170 mg, 0.80 mmol) was added. The mixture was then stirred at 50° C. for 4 h. before sat'd aqueous K2CO3 (˜50 mL) was added to the mixture. This solution was poured into a separatory funnel and extracted with CHCl3/isopropanol (5/1) (2×50 mL). The combined organic extract was dried over anhydrous Na2SO4, filtered, and conc. in vacuo affording the product. It was purified with Gilson (0.1% TFA in water:0.1% TFA in CAN=30% to 80%; UV absorption at 322) to yield the title compound as a yellow solid (94 mg, 77%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.96 (s, 1 H) 7.48 (d, 1 H) 7.41-7.34 (m, 1 H) 7.29 (t, 1 H) 3.67-3.58 (m, 2 H) 3.44-3.37 (m, 2 H) 3.03-2.78 (m, 5 H) 2.21 (brs, 1 H), 1.79 (d, 1 H) 1.61 (d, 6 H) 0.84-0.79 (m, 6 H). m/z 422.

Workup

  1. additionwas added
  2. additionwas added to the mixture
  3. additionThis solution was poured into a separatory funnel
  4. extractionextracted with CHCl3/isopropanol (5/1) (2×50 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customconc. in vacuo affording the product
  9. customIt was purified with Gilson (0.1% TFA in water:0.1% TFA in CAN=30% to 80%; UV absorption at 322)

Sources & evidence

ORD record
ord-d62caab8b5ed4aebbe276f53b7b26d52
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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