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

HRID 645939Notes

Reaction equation

HRID 645939 reaction equation
Br.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.[O:14]=[C:15]1[NH:24][CH:23]=[CH:22][C:21]2[N:20]=[C:19]([C:25]3[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=3)[C:18]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:17][C:16]1=2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].FC(F)(F)C(O)=O>CN(C=O)C.C(O)(=O)C.C(N(CC)CC)C>[OH:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[OH:12])[CH2:2][N:3]([CH2:29][C:28]1[CH:27]=[CH:26][C:25]([C:19]3[C:18]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[CH:17][C:16]4[C:15](=[O:14])[NH:24][CH:23]=[CH:22][C:21]=4[N:20]=3)=[CH:32][CH:31]=1)[CH2:4][CH2:5]2

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 27244601,2,3,4-Tetrahydro-6,7-isoquinolinediol hydrobromideHCID 5049666Sodium triacetoxyborohydrideHCID 592646194-(5-Oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzaldehyde

Product 1

HCID 119784632-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide (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 (1-13) as a yellow solid: 1H-NMR (500 MHz, d6 DMSO) δ 11.63 (s, 1H), 10.14 (bs, 1H), 9.06 (s, 1H), 8.41 (s, 1H), 7.51 (m, 5H), 7.35 (m, 3H), 7.26 (m, 2H), 6.70 (d, 2H, J=7.3 Hz), 6.58 (s, 1H), 6.51 (s, 1H), 4.42 (m, 2H), 4.10 (m, 2H), 3.20 (m, 2H), 2.90 (m, 2H) MS m/z (M+11) 476.

Workup

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

Sources & evidence

ORD record
ord-68301996faeb49fdb77374e9d8cbd0a6
Source dataset
uspto-grants-2010_04
Patent number
US07705014B2

Reaction notes

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