1,2-Dichloroethane → N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide

HRID 1025400Notes

Reaction equation

HRID 1025400 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:23])=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]3)[N:12]=2)=[CH:4][CH:3]=1.[N:24]1([CH2:31][CH2:32][CH2:33][NH:34][CH3:35])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CCN(C(C)C)C(C)C.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[N:24]1([CH2:31][CH2:32][CH2:33][N:34]([CH3:35])[C:20]([CH:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:11]3[N:12]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[O:9][C:10]=3[CH3:23])[CH2:15][CH2:16]2)=[O:22])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 206007003-(Azepan-1-yl)-N-methylpropan-1-amineHCID 209671331-((2-(4-Chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid

Product 1

HCID 45280367N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamideYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)piperidine-4-carboxylic acid (A-3, 70 mg, 0.52 mmole), 3-(azepan-1-yl)-N-methylpropan-1-amine (20 mg) and DIPEA (0.05 mL) in DMF (2 mL) was added EDC (35 mg). The reaction solution was stirred at room temperature for 12 hours. The reaction was diluted with EtOAc (30 mL). The organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL) and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified through chromatography (CH2Cl2:MeOH 10:1) to give N-(3-(azepan-1-yl)propyl)-1-((2-(4-chlorophenyl)-5-methyloxazol-4-yl)methyl)-N-methylpiperidine-4-carboxamide (42 mg, 82%). H1NMR (300 MHz, CDCl3), ppm: 7.97 (d, 2H), 7.48 (d, 2H), 3.80 (m, 1H), 3.63 (m, 2H), 3.45 (m, 2H), 3.31-3.14 (m, 7H), 2.75 (s, 3H), 2.44 (m, 4H), 2.01 (m, 2H), 1.85 (m, 10H), 1.30 (m, 2H), 1.26 (m, 2H). MS (ESI+) M/z: 487, 489 (M+H).

Workup

  1. washThe organic layer was washed with saturated sodium bicarbonate (10 mL), water (10 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified through chromatography (CH2Cl2:MeOH 10:1)

Sources & evidence

ORD record
ord-7d7fa4203dab4a30825dd48bfeee0467
Source dataset
uspto-grants-2014_05
Patent number
US08729081B2

Reaction notes

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