Triethylamine → HCID 11349491, compound

HRID 747990Notes

Reaction equation

HRID 747990 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.[CH:22]1([CH2:28][CH2:29][NH2:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CCN(CC)CC.[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[CH:22]1([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)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2000082-Cyclohexylethanamine hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×

Product 1

HCID 11349491HCID 11349491, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Using a method similar to Example 14, using 6-(1-oxo-indan-5-yloxy)-nicotinamide (Intermediate 4, 536 mg, 2.00 mmol), 2-cyclohexylethylamine HCl ((Synthesis (1983), (5), 388-9), 393 mg, 2.40 mmol), Et3N (243 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 (628 mg) as a yellow solid. Mass spectrum (ion spray): m/z=380 (M+1); 1HNMR (CDCl3): 8.59 (s, 1H), 8.15 (d, 1H), 7.38 (d, 1H), 6.99 (s, 1H), 6.95 (d, 1H), 6.94 (d, 1H), 5.89 (br. s, 2H), 4.24 (t, 1H), 3.01 (m, 1H), 2.82 (m, 1H), 2.75 (t, 2H), 2.45 (m, 1H), 1.88 (m, 1H), 1.74-1.62 (m, 5H), 1.43 (m, 2H), 1.38-1.13 (m, 4H), 0.93 (m, 2H).

Sources & evidence

ORD record
ord-a12d1a77374a4c09ba2a1a4770155b81
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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