Ethyl Acetate → Tert-butyl 2-amino-4-(4-amino-3-hydroxyphenyl)-6-[2-[(4-methoxybenzyl)oxy]-6-(2-methylbutoxy)phenyl]nicotinate

HRID 2218264Notes

Reaction equation

HRID 2218264 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[C:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[CH:19][CH:18]=[CH:17][C:16]=2[O:31][CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH:12]=[C:11]([C:36]2[CH:41]=[CH:40][C:39]([N+:42]([O-])=O)=[C:38]([OH:45])[CH:37]=2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[C:46](OCC)(=O)C>C1COCC1.[Pd]>[NH2:1][C:2]1[N:14]=[C:13]([C:15]2[C:16]([O:31][CH2:32][CH:33]([CH3:46])[CH2:35][CH3:34])=[CH:17][CH:18]=[CH:19][C:20]=2[O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[CH:12]=[C:11]([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([OH:45])[CH:37]=2)[C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69145610Tert-butyl 2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-(3-hydroxy-4-nitrophenyl)nicotinate

Product 1

HCID 69147205Tert-butyl 2-amino-4-(4-amino-3-hydroxyphenyl)-6-[2-[(4-methoxybenzyl)oxy]-6-(2-methylbutoxy)phenyl]nicotinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-amino-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-(3-hydroxy-4-nitrophenyl)nicotinate (2.32 g, 3.78 mmol) in ethyl acetate (15.0 mL) and THF (15.0 mL) was hydrogenated at 1 atm in the presence of palladium on charcoal (10%, 0.10 g) overnight. The resulting mixture was filtered on Celite and washed with ethyl acetate and THF. The combined filtrate was concentrated under reduced pressure to give tert-butyl 2-amino-4-(4-amino-3-hydroxyphenyl)-6-[2-[(4-methoxybenzyl)oxy]-6-(2-methylbutoxy)phenyl]nicotinate. (2.21 g, 100%); LC-MS (m/z=584, M+1)

Workup

  1. filtrationThe resulting mixture was filtered on Celite
  2. washwashed with ethyl acetate and THF
  3. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6d8e03fe791d438c90846cf99db778af
Source dataset
uspto-grants-2008_08
Patent number
US07410986B2

Reaction notes

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