Acetic Acid → (+/-)-6-[4-(3-Phenyl-azepan-1-ylmethyl)-phenoxy]-nicotinamide

HRID 228226Notes

Reaction equation

HRID 228226 reaction equation
C(O)(=O)/C=C/C(O)=O.[C:9]1([CH:15]2[CH2:21][CH2:20][CH2:19][CH2:18][NH:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:22]([C:24]1[CH:39]=[CH:38][C:27]([O:28][C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][N:30]=2)=[CH:26][CH:25]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[C:9]1([CH:15]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:22][C:24]3[CH:39]=[CH:38][C:27]([O:28][C:29]4[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][N:30]=4)=[CH:26][CH:25]=3)[CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 568514226-(4-Formylphenoxy)pyridine-3-carboxamide2×HCID 131726912HCID 131726912, compound

Product 1

HCID 59730169(+/-)-6-[4-(3-Phenyl-azepan-1-ylmethyl)-phenoxy]-nicotinamideYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Using a method similar to Example 345, using 3-phenyl-azepane fumaric acid salt (0.122 g, 0.419 mmol), 6-(4-formyl-phenoxy)-nicotinamide (compound of example 332, step 1) (0.100 g, 0.415 mmol), sodium triacetoxyborohydride (0.129 g, 0.609 mmol), and acetic acid (0.034 mL, 0.594 mmol) in 1,2-dichloroethane (8.0 mL) provides 0.154 g (93%) of the title compound as a white solid: high resolution mass spectrum (electrospray): m/z calc for C25H28N3O2 402.2182, found 402.2199; 1H NMR (DMSO-d6): 8.61 (d, 1H, J=1.8 Hz), 8.25 (dd, 1H, J=2.6, 8.8 Hz), 8.02 (s, 1H), 7.47 (s, 1H), 7.38 (d, 2H, J=8.4 Hz), 7.27-7.02 (m, 5H), 3.70 (d, 1H, J=13.5 Hz), 3.64 (d, 1H, J=13.5 Hz), 2.89-2.63 (m, 5H), 1.81-1.59 (m, 6H).

Sources & evidence

ORD record
ord-4fc2685f85f9460bbf080502cbe3fcd6
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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