Furfural → HCID 69006889, compound

HRID 1432430Notes

Reaction equation

HRID 1432430 reaction equation
C(O[BH-](O[C:11](=[O:13])[CH3:12])OC(=O)C)(=O)C.[Na+].[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][N:32](S(CC5C=CC=CC=5)(=O)=O)[CH2:31][CH2:30]4)[NH:26][C:25]=3[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:23][C:18]=2[O:17][CH2:16]1.O1C=C[CH:53]=[C:52]1[CH:56]=O>ClCCl>[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]3[N:28]=[C:27]([CH:29]4[CH2:34][CH2:33][N:32]([C:31]5[O:13][CH:11]=[CH:12][CH:30]=5)[CH:52]([CH3:56])[CH2:53]4)[NH:26][C:25]=3[C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][N:46]=3)=[CH:23][C:18]=2[O:17][CH2:16]1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 5049666Sodium triacetoxyborohydrideHCID 10345947HCID 10345947, compound

Product 1

HCID 69006889HCID 69006889, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.030 g, 0.14 mmol) was added to a solution of 2-(5-benzo[1,3]dioxol-5-yl-2-piperidin-4-yl-3H-imidazol-4-yl)-pyridine (0.035 g, 0.10 mmol; prepared as described in Example 11) and furan-2-carbaldehyde (0.0083 mL, 0.10 mmol) in dichloromethane (5 mL). The mixture was stirred at room temperature for 18 hours and was filtered and concentrated. HPLC purification eluting with acetonitrile:water gave 0.010 g (23%) of the title compound as a yellow solid. MS (ESP+) m/z 429.1. 1H NMR (400 MHz, DMSO-d6) δ 8.67 (m, 1H), 7.87 (m, 2H), 7.44 (m, 2H), 7.09 (m, 3H), 6.73 (d, 1H, J=3.2 Hz), 6.60 (m, 1H), 6.12 (s, 2H), 4.45 (s, 2H), 3.54 (m, 2H), 3.26 (m, 1H), 3.11 (m, 2H), 2.33 (m, 2H), 2.06 (m, 2H).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customHPLC purification
  4. washeluting with acetonitrile

Sources & evidence

ORD record
ord-5499b9fb1c2843ef93eecaf0153be3b0
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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