Thiopheneethanamine → 6-[1-(2-Thiophen-2-yl-ethylamino)-indan-5-yloxy]-nicotinamide

HRID 422228Notes

Reaction equation

HRID 422228 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.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][CH2:27][NH2:28].[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH2:26][CH2:27][NH:28][CH: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

Participants

5

Reactant 3

HCID 116521ThiopheneethanamineHCID 5003444Sodium cyanoborohydrideHCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 113149836-[1-(2-Thiophen-2-yl-ethylamino)-indan-5-yloxy]-nicotinamideYield 51.7%

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, 268 mg, 1.00 mmol), 2-thiopheneethylamine (152 mg, 1.20 mmol), Ti(iPrO)4 (568 mg, 2.00 mmol), TiCl4 (1.0M/DCM, 2.00 ml, 2.00 mmol), and NaBH3CN (125 mg, 2.00 mmol) gives the title compound (196 mg) as a white solid. Mass spectrum (ion spray): m/z=380 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.35 (d, 1H), 7.16 (d, 1H); 6.99 (s, 1H), 6.96-6.93 (m, 3H), 6.86 (d, 1H), 5.81 (br. s, 2H), 4.28 (t, 1H), 3.11-2.96 (m, 5H), 2.83 (m, 1H), 2.46 (m, 1H), 1.87 (m, 1H).

Sources & evidence

ORD record
ord-3d37db3a3d1a408b85c8bdd509fcdc64
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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