Acetic Acid → HCID 178480125, compound

HRID 605000Notes

Reaction equation

HRID 605000 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]([CH:35]=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(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[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]([CH2:35][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 178480125HCID 178480125, 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 dihydrochloride (142 mg, 10.47 mmol) and 4-(6-methyl-5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (5141 mg, 0.415 mmol) in dry DMF (1.5 mL) was added triethylamine (0.21 mL, 1.5 mmol). After stirring for 10 minutes acetic acid (0.26 mL, 4.5 mmol) was added and the mixture was stirred at room temperature over night. Then sodium triacetoxy borohydride (110 mg, 0.52 mmol) was added in one portion and stirred for eight hours. After monitoring by LC/MS determined the reaction was not complete additional sodium triacetoxy borohydride (46 mg, 0.21 mmol)) were added and the reaction was stirred over night. This reaction mixture was adsorbed on silica gel and purified by column chromatography eluting with 1-7% methanol/ethyl acetate (sat'd NH3). The appropriate fractions were combined, the solvents removed in vacuo, and the residue digested in acetonitrile containing a little methanol to give pure title compound. 1H NMR (500 MHz, CDCl3): δ 8.69 (1H, s), 8.65 (1H, d, J=4.4 Hz), 8.15 (1H, d, J=7.8 Hz), 7.83 (1H, t, J=7.6 Hz), 7.31-7.39 (5H, m), 7.22-7.25 (6H, m), 6.86 (1H, d, J=6.5 Hz), 3.66 (3H, s), 3.53 (2H, s), 2.95 (2H, br d, J=10.7 Hz), 2.85 (1H, m), 2.06-2.15 (4H, m), 1.92-2.01 (2H, m). m/e (m+1): 554.3, 277.9 [(m+2)/2].

Workup

  1. additionwas added
  2. stirringstirred for eight hours
  3. additionwere added
  4. stirringthe reaction was stirred over night
  5. custompurified by column chromatography
  6. washeluting with 1-7% methanol/ethyl acetate (sat'd NH3)
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-b6b799212b9d43eb82251d43ef42a841
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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