3-Chlorophenethylamine → 6-{1-[2-(3-Chloro-phenyl)-ethylamino]-indan-5-yloxy}-nicotinamide

HRID 422230Notes

Reaction equation

HRID 422230 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=3)=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH2:30])[CH:25]=[CH:26][CH:27]=1.[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[Cl:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][NH:30][CH:2]2[C:10]3[C:5](=[CH:6][C:7]([O:11][C:12]4[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=4)=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1393813-ChlorophenethylamineHCID 5003444Sodium cyanoborohydrideHCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 113842576-{1-[2-(3-Chloro-phenyl)-ethylamino]-indan-5-yloxy}-nicotinamideYield 60.3%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 1, using 6-(1-oxo-indan-5-yloxy)nicotinamide (Intermediate 4, 905 mg, 3.00 mmol), 2-(3-chlorophenyl)ethylamine (560 mg, 3.60 mmol), Ti(iPrO)4 (1.70 g, 6.00 mmol), TiCl4 (1.0M/DCM, 6.00 ml, 6.00 mmol), and NaBH3CN (377 mg, 6.00 mmol) gives the title compound (738 mg) as a white solid. Mass spectrum (ion spray): m/z=408 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.31 (d, 1H), 7.25-7.18 (m, 3H), 7.11 (d, 1H), 6.98-6.93 (m, 3H), 5.89 (br. s, 2H), 4.26 (t, 1H), 3.03-2.96 (m, 3H), 2.87-2.78 (m, 3H), 2.44 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-e7f8a26b4661458aba6a316022e21b86
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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