Acetic Acid → HCID 178514862, compound

HRID 605003Notes

Reaction equation

HRID 605003 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][N:10]=2)[CH2:5][CH2:4]1.[CH3:20][N:21]1[CH:30]=[CH:29][C:28]2[N:27]=[C:26]([C:31]3[CH:38]=[CH:37][C:34](C=O)=[CH:33][CH:32]=3)[C:25]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:24][C:23]=2[C:22]1=[O:45].C(N(CC)CC)C.[C:53](O)(=[O:55])C.[C:57](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[OH:55][CH2:53][CH2:20][N:21]1[CH:30]=[CH:29][C:28]2[N:27]=[C:26]([C:31]3[CH:38]=[CH:37][C:34]([CH2:57][N:3]4[CH2:8][CH2:7][CH:6]([C:9]5[N:13]=[C:12]([C:14]6[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=6)[NH:11][N:10]=5)[CH2:5][CH2:4]4)=[CH:33][CH:32]=3)[C:25]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:24][C:23]=2[C:22]1=[O:45]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 866249424-(6-Methyl-5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehydeHCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

Product 1

HCID 178514862HCID 178514862, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine dihydro-chloride (21 mg, 0.07 mmol) and 4-(6-methyl-5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (17 mg, 0.046 mmol) in dry DMF (1.0 mL) was added triethyl-amine (25 mL, 0.18 mmol). After stirring for 10 minutes acetic acid (30 μL, 0.53 mmol) was added and the mixture was stirred at room temperature over night. Then sodium triacetoxy borohydride (17 mg, 0.08 mmol) was added in one portion. After monitoring by LC/MS it was determined the reaction was not complete and additional sodium triacetoxy borohydride (5 mg, 0.02 mmol)) were added and the reaction was stirred over night. This reaction mixture was concentrated to a smaller volume and adsorbed on silica gel and purified by column chromatography eluting with 20-100% ethyl acetate and then 0.5-9% methanol/ethyl acetate (sat'd NH3). The appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with diethyl ether to give pure title compound as a pale yellow solid. 1H NMR (500 MHz, CDCl3): δ 8.69 (1H, s), 8.64 (1H, d, J=4.4 Hz), 8.14 (1H, d, J=7.5 Hz), 7.83 (1H, t, J=7.5 Hz), 7.35-7.41 (5H, m), 7.21-7.28 (6H, m), 6.89 (1H, d, J=7.6 Hz), 4.24 (2H, t, J=4.8 Hz), 4.04 (2H, t, J=4.6 Hz), 3.58 (2H, vbr s), 3.00 (2H, vbr s), 2.86 (1H, m), 2.02-2.17 (4H, m). m/e (m+1): 584.1, 292.7 [(m+2)/2].

Workup

  1. additionwas added
  2. stirringthe reaction was stirred over night
  3. concentrationThis reaction mixture was concentrated to a smaller volume
  4. custompurified by column chromatography
  5. washeluting with 20-100% ethyl acetate
  6. customthe solvents removed in vacuo
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-743f26b9c78743699ffafaa9d9b7951d
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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