Sodium triacetoxyborohydride → HCID 178489119, compound

HRID 605015Notes

Reaction equation

HRID 605015 reaction equation
[O:1]=[C:2]1[NH:11][CH:10]=[CH:9][C:8]2[N:7]=[C:6]([C:12]3[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=3)[C:5]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:4][C:3]1=2.FC(F)(F)C(O)=O.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[NH:45][C:44]([CH:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)=[N:43][N:42]=2)=[CH:37][N:36]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCN(CC)CC.CN(C=O)C.CC(O)=O>[CH3:33][O:34][C:35]1[N:36]=[CH:37][C:38]([C:41]2[NH:45][C:44]([CH:46]3[CH2:51][CH2:50][N:49]([CH2:16][C:15]4[CH:14]=[CH:13][C:12]([C:6]5[C:5]([C:20]6[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=6)=[CH:4][C:3]6[C:2](=[O:1])[NH:11][CH:10]=[CH:9][C:8]=6[N:7]=5)=[CH:19][CH:18]=4)[CH2:48][CH2:47]3)=[N:43][N:42]=2)=[CH:39][CH:40]=1

Participants

7

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehydeHCID 178489118HCID 178489118, compound

Product 1

HCID 178489119HCID 178489119, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a dry flask was added 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (308 mg, 0.94 mmol) and 2-methoxy-5-(5-piperidin-4-yl-4H-1,2,4-triazol-3-yl)pyridine trifluoroacetate (350 mg, 0.94 mmol) in 5% NEt3:DMF (5 mL). The solution was stirred for 15 min. then 5% AcOH:DMF (10 mL) was added. This was stirred for 1 h and sodium triacetoxyborohydride was added and the reaction mixture was stirred for 16 h at room temperature. The mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution and then extracted (×3) with CH2Cl2, the organic layers combined and dried over anhydrous Na2SO4. This was filtered, concentrated and purified by silica gel chromatography (2-4% MeOH in CH2Cl2) to give 2-[4-({4-[5-(6-methoxypyridin-3-yl)-4H-1,2,4-triazol-3-yl]piperidin-1-yl}methyl)phenyl]-3-phenyl-1,6-naphthyridin-5(6H)-one. NMR (MeOD): δ 8.73-8.72 (1H, d, J=3 Hz), 8.52 (1H, s) 8.25-824 (1H, d, J=3 Hz), 7.43-7.41 (1H, d, J=6), 7.33-714 (1H, m), 6.80 (2H, m), 3.93 (3H, s), 3.6 (2H, s), 3.02-2.98 (2H, m), 2.86 (1H, m), 2.27 (2H, m), 2.05 (2H, m), 1.93 (3H, m). m/e (m+1): 570.1.

Workup

  1. stirringThis was stirred for 1 h
  2. stirringthe reaction mixture was stirred for 16 h at room temperature
  3. customThe mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate solution
  4. extractionextracted (×3) with CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationThis was filtered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography (2-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f7865adebfa940b6b838ee1d45db7c04
Source dataset
uspto-grants-2011_03
Patent number
US07910561B2

Reaction notes

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