HCID 18761421, compound → CHEBI:82669

HRID 431736Notes

Reaction equation

HRID 431736 reaction equation
C(OC([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH2:22][CH2:23][Cl:24])=[C:14]([NH:25][C:26]([C:28]2[NH:29][C:30]3[C:35]([CH:36]=2)=[CH:34][C:33]([O:37][CH3:38])=[C:32]([O:39][CH3:40])[C:31]=3[O:41][CH3:42])=[O:27])[CH:13]=1)=O)C1C=CC=CC=1>C1COCC1.[Pd]>[Cl:24][CH2:23][CH2:22][C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([NH2:11])=[CH:13][C:14]=1[NH:25][C:26]([C:28]1[NH:29][C:30]2[C:35]([CH:36]=1)=[CH:34][C:33]([O:37][CH3:38])=[C:32]([O:39][CH3:40])[C:31]=2[O:41][CH3:42])=[O:27]

Participants

4

Reactant 1

HCID 18761421HCID 18761421, compound

Product 1

HCID 9825161CHEBI:82669Yield 18.1%

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 chloride (60.0 mg, 0.10 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (50 mg) 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. Preparative TLC (50% AcOEt-Petroleum ether) afforded 4-(2-chloroethyl)-3-(5,6,7-trimethoxyindole-2-carboxamido)-1-naphthylamine (8.2 mg, 18%) as a pale yellow solid. M.p. 182° C. (decomp.); 1H NMR (CDC3, 500 MHz) δ 9.40 (s, 1H), 8.54 (s, 1H), 7.85 (d, 8.5, 1H), 7.83 (d, 8.0, 1H), 7.53 (t, 7.5, 1H), 7.46 (t, 8.5, 1H), 7.32 (s, 1H), 6.97 (s, 1H), 6.86 (s, 1H), 4.25 (brs, 2H) 4.08 (s, 3H), 3.98 (t, 6.5, 2H), 3.95 (s, 3H), 3.92 (s, 3H), 3.54 (t, 6.5, 2H); IR (neat) 3326, 2927, 2856, 1626, 1590, 1536, 1501, 1466, 1408, 1302, 1240, 1107, 1049, 1000, 907, 832, 756 cm−1. FAB HRMS (NBA) m/z 454.1549 (M+H+, C24H24ClN3O4 requires 454.1534). Anal. Calcd. For C24H24N3O4Cl.1/2H2O: C, 62.20; H, 5.40; N, 9.07. Found: C, 62.39; H, 5.71; N, 8.68.

Workup

  1. filtrationThe suspension was filtered over Celite
  2. concentrationthe filtrate was concentrated in reduced pressure

Sources & evidence

ORD record
ord-f09000002d96401baae4f897cb68a2a8
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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