HCID 18761407, compound → HCID 10135220, compound

HRID 431741Notes

Reaction equation

HRID 431741 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])=[CH:32][CH:31]=3)=[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])=[CH:32][CH:31]=2)=[O:27]

Participants

4

Reactant 1

HCID 18761407HCID 18761407, compound

Product 1

HCID 10135220HCID 10135220, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethyl chloride (68 mg, 0.13 mmol) in THF (10 mL) was added to a suspension of 10% Pd/C (100 mg) in chilled THF (10 mL) and the suspension was hydrogenated under H2 atmosphere at room temperature overnight. The suspension was filtered over Celite and the filtrate was concentrated in reduced pressure. The residue was crystallized with diethylether to yield 4-(2-Chloroethyl)-3-(5-methoxyindole-2-carboxamido)-1-naphthylamine (40 mg, 78%) as a white solid: mp 228° C. (decomp.); 1H NMR (DMSO-d6, 500 MHz) δ 9.95 (s, 1H), 8.11 (d, 8.5, 1H), 7.96 (d, 8.0, 1H), 7.52 (t, 7.0, 1H), 7.41 (t, 7.0, 1H), 7.35 (d, 9.0, 1H), 7.28 (s, 1H), 7.13 (s, 1H), 6.89 (d, 9.0, 1H), 6.67 (s, 1H) 5.83 (s, 2H), ), 3.77 (s, 3H), 3.73 (t, 8.0, 2H), 3.37 (t, 8.0, 2H); ); FABMS (NBA) m/z 394 (M+H+); IR (nujol) νmax 3296, 1652, 1592, 1533, 1462, 1260, 1094, 1020, 800 cm−1.

Workup

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

Sources & evidence

ORD record
ord-90229f03cf3e44a6aa8784de6ef3cfaf
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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