HCID 18761417, compound → HCID 11282958, compound

HRID 431737Notes

Reaction equation

HRID 431737 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17]C(OCC2C=CC=CC=2)=O)=[CH:9][C:8]=1[NH:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([O:40][CH3:41])=[C:35]([O:42][CH3:43])[C:34]=2[O:44][CH3:45])=[O:30])(=[O:3])[CH3:2]>C1COCC1.[Pd]>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH2:17])=[CH:9][C:8]=1[NH:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([O:40][CH3:41])=[C:35]([O:42][CH3:43])[C:34]=2[O:44][CH3:45])=[O:30])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18761417HCID 18761417, compound

Product 1

HCID 11282958HCID 11282958, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.1 g, 0.16 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (0.1 g) in chilled THF (10 mL) and the suspension was hydrogenated under H2 atmosphere at room temperature for 3 days. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure. The residue was crystallized with diisopropylether to yield 2-[4-amino-2-(5,6,7-trimethoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.064 g, 84%) as a white solid: mp 182-186° C. (decomp.); 1H NMR (CDCl3, 500 MHz) δ 9.40 (s, 1H), 8.65 (s, 1H), 7.94 (d, 8.5, 1H), 7.86 (d, 8.5, 1H), 7.57 (s, 1H), 7.55 (t, 8.0, 1H), 7.46 (t, 8.0, 1H), 7.19 (brs, 1H), 6.88 (s, 1H), 4.39 (t, 7.0, 2H), 4.23 (brs, 2H), 4.10 (s, 3H), 3.96 (s, 3H), 3.93 (s, 3H), 3.41 (t, 7.0, 2H), 2.10 (s, 1.5, 3H); FABMS (NBA) m/z 478 (M+H+), IR (neat) νmax 3341, 1727, 1639, 1591, 1536, 1505, 1466, 1410, 1304, 1243, 1106, 1046, 758 cm−1.

Workup

  1. filtrationThe suspension was filtered over Celite
  2. concentrationthe filtrate was concentrated in reduced pressure
  3. customThe residue was crystallized with diisopropylether

Sources & evidence

ORD record
ord-6c1f733af1bc49cbaae67afaea091c5b
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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