Triethylamine → HCID 11271122, compound

HRID 747979Notes

Reaction equation

HRID 747979 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.[CH3:22][O:23][C:24]1[C:32]2[C:31]([CH2:33][CH2:34][NH2:35])=[CH:30][S:29][C:28]=2[CH:27]=[CH:26][CH:25]=1.CCN(CC)CC.[BH3-]C#N.[Na+]>Cl[Ti](Cl)(Cl)Cl>[CH3:22][O:23][C:24]1[C:32]2[C:31]([CH2:33][CH2:34][NH:35][CH:2]3[C:10]4[C:5](=[CH:6][C:7]([O:11][C:12]5[CH:20]=[CH:19][C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=5)=[CH:8][CH:9]=4)[CH2:4][CH2:3]3)=[CH:30][S:29][C:28]=2[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 597506396-(1-Oxo-indan-5-yloxy)-nicotinamide2×HCID 66673466HCID 66673466, compound

Product 1

HCID 11271122HCID 11271122, compoundYield 49.9%

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, 97 mg, 0.362 mmol), 2-(4-methoxy-benzo[b]thiophen-3-yl)-ethylamine HCl salt (J. Heterocycl. Chem. (1973), 10(3), 297-305, 93 mg, 0.435 mmol), Et3N (44 mg, 0.435 mmol), Ti(iPrO)4 (206 mg, 0.725 mmol), TiCl4 (1.0M/DCM, 0.725 ml, 0.725 mmol), and NaBH3CN (45 mg, 0.725 mmol) gives the title compound (83 mg) as a light yellow solid. Mass spectrum (ion spray): m/z=460 (M+1); 1HNMR (CDCl3): 8.58 (s, 1H), 8.15 (d, 1H), 7.42 (d, 1H), 7.33 (d, 1H), 7.25 (t, 1H), 7.02 (s, 1H), 6.98 (s, 1H), 6.94-6.91 (m, 2H), 6.75 (d, 1H), 5.82 (br. s, 2H), 4.30 (t, 1H), 3.91 (s, 3H), 3.29 (t, 2H), 3.09 (m, 2H), 3.01 (m, 1H), 2.83 (m, 1H), 2.45 (m, 1H), 1.90 (m, 1H).

Sources & evidence

ORD record
ord-a6859cf6d8fa478f8c537df85c866ee7
Source dataset
uspto-grants-2008_07
Patent number
US07399774B2

Reaction notes

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