Methyl iodide → N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-propionamide

HRID 32131Notes

Reaction equation

HRID 32131 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)(=[O:20])=[O:19])[CH2:8][CH2:7][CH2:6]2)=[O:2].[C:38](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([NH:13][C:14](=[O:37])[CH2:15][CH:16]([N:17]([CH3:38])[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=1)(=[O:20])=[O:19])[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[CH2:8][CH2:7][CH2:6]2)=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 86598510N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide

Product 1

HCID 86598509N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-propionamideYield 106.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The aldehyde, N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionamide (0.11 g), was stirred in dry DMF (5 mL) with sodium carbonate (0.2 g) and methyl iodide (0.2 mL) at RT for 3 days. Aqueous workup gave the crude product, N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-propionamide (0.12 g). MS: 545.1 (M+1). This aldehyde (0.12 g) was converted to 3-[methyl-(3-trifluoromethyl-benzenesulfonyl)-amino]-3-phenyl-N-(6-piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionamide using the general reductive amination conditions (amine, NaBH(OAc)3, RT, DCE) described earlier in this application. MS: 614.1 (M+1).

Sources & evidence

ORD record
ord-7d82403326aa429a9d950530b58b338e
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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