Acetic Acid → HCID 86608130, compound

HRID 130768Notes

Reaction equation

HRID 130768 reaction equation
[C:1](O)(=O)/[CH:2]=[CH:3]/[C:4]([OH:6])=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.C(C1C=CC(O[C:29]2[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][N:30]=2)=CC=1)=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:41].[Na+].[C:54](O)(=O)C>ClCCCl>[C:9]1([CH:15]2[CH2:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:54][C:1]3[CH:2]=[CH:3][C:4]([O:6][C:31]4[N:30]=[CH:29][CH:37]=[CH:36][C:32]=4[C:33]([NH2:35])=[O:34])=[CH:41][CH:40]=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 1317269123-Phenyl-azepane fumaric acid salt

Product 1

HCID 86608130HCID 86608130, compoundYield 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, 8H), 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-a73710c0b1494c10969e676c9ba15754
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

Loading…