Acetic Acid → HCID 58213748, compound

HRID 340200Notes

Reaction equation

HRID 340200 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-253408b8e5794dcb9b2da4270c7a3634
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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