Acetic Acid → HCID 58213748, compound

HRID 1259068Notes

Reaction equation

HRID 1259068 reaction equation
[Si]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[C:12]([NH2:23])[N:13]=[C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]3=2)[N:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1>[NH2:23][C:12]1[C:11]2[NH:10][C:9](=[O:8])[CH:18]=[CH:17][C:16]=2[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 671176883-(Tert-butyldimethylsilyloxy)benzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 58213748HCID 58213748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(tert-butyldimethylsilyloxy)benzo[f][1,7]naphthyridin-5-amine (from step 4) (1.0 eq.) in tetrahydrofuran (0.05 M) was added tetra-n-butylammonium fluoride (TBAF) (1.0 eq.) and acetic acid (1.0 eq.). The reaction was stirred for 15 minutes, and then concentrated en vacuo. The crude residue was suspended in water and neutralized by addition of saturated aqueous NaHCO3 solution to pH 7. The solids were filtered, washed with acetone, and dried to give 5-aminobenzo[f][1,7]naphthyridin-3(4H)-one. 1H NMR (DMSO d-6): δ 8.59 (d, 1H), 8.20 (d, 1H), 7.49 (d, 1H), 7.37-7.41 (dd, 1H), 7.23-7.27 (dd, 1H), 6.88 (br, 2H), 6.79 (d, 1H). LRMS [M+H]=212.1

Workup

  1. concentrationconcentrated en vacuo
  2. additionneutralized by addition of saturated aqueous NaHCO3 solution to pH 7
  3. filtrationThe solids were filtered
  4. washwashed with acetone
  5. customdried

Sources & evidence

ORD record
ord-3ff4d3188a044bbca2a4725bdf5f7428
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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