Hydrochloric Acid → 2-[4-(1-amino-1-methylethyl)phenyl]-3-(2-thienyl)-1,6-naphthyridin-5(6H)-one

HRID 732875Notes

Reaction equation

HRID 732875 reaction equation
C[O:2][C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[C:7]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([NH2:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=1)=[N:8]2.Cl>C1COCC1>[NH2:22][C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:7]2[C:6]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:5][C:4]3[C:3](=[O:2])[NH:12][CH:11]=[CH:10][C:9]=3[N:8]=2)=[CH:18][CH:17]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690592742-{4-[5-Methoxy-3-(2-thienyl)-1,6-naphthyridin-2-yl]phenyl}propan-2-amine

Product 1

HCID 118549652-[4-(1-amino-1-methylethyl)phenyl]-3-(2-thienyl)-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{4-[5-methoxy-3-(2-thienyl)-1,6-naphthyridin-2-yl]phenyl}propan-2-amine (2-6, 66 mg, 0.176 mmol) in THF (10 mL) was added concentrated HCl (1 mL) and stirred for 5 h at rt. The volatiles were evaporated in vacuo and the residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give the title compound as an off-white solid. LRMS m/z (M+1) Calcd: 362.1,. Found 362.2.

Workup

  1. customThe volatiles were evaporated in vacuo
  2. customthe residue was partitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a54003a015341c3b62e272e9fcddc62
Source dataset
uspto-grants-2009_09
Patent number
US07589068B2

Reaction notes

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