Thiopheneethanamine → HCID 11383823, compound

HRID 747980Notes

Reaction equation

HRID 747980 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:5]=[CH:4][C:3]1=2.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][CH2:28][NH2:29].[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[CH2:27][CH2:28][NH:29][CH:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 116521ThiopheneethanamineHCID 5003444Sodium cyanoborohydrideHCID 59750647HCID 59750647, compound2×

Product 1

HCID 11383823HCID 11383823, compound

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 1, using 6-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-nicotinamide (Intermediate 2, 546 mg, 2.00 mmol), 2-thiopheneethylamine (305 mg, 2.40 mmol), Ti(iPrO)4 (1.14 g, 4.00 mmol), TiCl4 (1.0M/DCM, 4.00 ml, 4.00 mmol), and NaBH3CN (251 mg, 4.00 mmol) gives the title compound (491.mg) as a light yellow solid. Mass spectrum (ion spray): m/z=394 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.36 (d, 1H), 7.15 (d, 1H), 6.95-6.89 (m, 3H), 6.85 (m, 2H), 5.87 (br. s, 2H), 3.81 (t, 1H), 3.12-3.02 (m, 3H), 2.98 (m, 1H), 2.83-2.68 (m, 2H), 1.98-1.82 (m, 3H), 1.73 (m, 1H).

Sources & evidence

ORD record
ord-544cb2d407f949208fa5d226fcb417a4
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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