Dimethylformamide → 2-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one trifluoroacetate

HRID 645938Notes

Reaction equation

HRID 645938 reaction equation
O1[C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3](O)=N1.[O:11]=[C:12]1[NH:21][CH:20]=[CH:19][C:18]2[N:17]=[C:16]([C:22]3[CH:29]=[CH:28][C:25](C=O)=[CH:24][CH:23]=3)[C:15]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][C:13]1=2.C(O[BH-](O[C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].CN([CH:60]=[O:61])C>C(O)(=O)C.C(N(CC)CC)C>[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[OH:61][C:60]1[CH:3]=[C:4]2[C:5](=[CH:47][C:46]=1[OH:48])[CH2:6][N:7]([CH2:51][C:25]1[CH:24]=[CH:23][C:22]([C:16]3[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:14][C:13]4[C:12](=[O:11])[NH:21][CH:20]=[CH:19][C:18]=4[N:17]=3)=[CH:29][CH:28]=1)[CH2:8][CH2:9]2

Participants

8

Reactant 5

HCID 6228Dimethylformamide2×HCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehydeHCID 178518978HCID 178518978, compound

Product 1

HCID 119786922-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one trifluoroacetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolvent

Procedure

To 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-3-ol (46 mg) and 4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde (130 mg) in DMF (0.5 mL) was added, triethylamine (64 μL), this solution was stirred for 15 minutes then acetic acid (117 μL) was added and the solution stirred for 3 hours. Sodium triacetoxyborohydride (48 mg) in DMF (0.5 mL) was then added. The reaction mixture was stirred overnight, trifluoroacetic acid (100 μL) was added purified by HPLC to give 2-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one trifluoroacetate (salt) as a yellow solid: 1H-NMR (500 MHz, CD3OD) δ 8.65 (s, 1H), 7.51 (m, 3H), 7.45 (d, 2H, J=8.2 Hz), 7.23 (m, 3H), 7.20 (m, 2H), 6.88 (d, 2H, J=7.7 Hz), 4.24 (m, 2H), 3.97 (m, 2H), 3.29 (m, 2H), 2.66 (m, 2H). MS m/z (M+H) 451.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-1c38c5fe7c7344ecbbe092fd0213b6d6
Source dataset
uspto-grants-2010_04
Patent number
US07705014B2

Reaction notes

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