2,4-Dichlorobenzoyl chloride → HCID 68690416, compound

HRID 1169842Notes

Reaction equation

HRID 1169842 reaction equation
[NH2:1][CH2:2][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:23][C:24]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>>[Cl:23][C:24]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:25]=1[C:26]([NH:1][CH2:2][C:3]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:27]

Participants

3

Reactant 2

HCID 666452,4-Dichlorobenzoyl chlorideHCID 68693818HCID 68693818, compound

Product 1

HCID 68690416HCID 68690416, compound

Procedure

tert-Butyl 4-(aminomethyl)-4-(6-fluoropyridin-2-yl)piperidine-1-carboxylate (0.82 mmol) was acylated with 2,4-dichlorobenzoyl chloride (0.12 mL, 0.82 mmol) using the method described in example 8-1 to afford the desired product: tert-butyl 4-{[(2,4-dichlorobenzoyl)amino]methyl}-4-(6-fluoropyridin-2-yl)piperidine-1-carboxylate: 1H NMR δ (ppm)(CDCl3): 7.81 (1 H, q, J=8.0 Hz), 7.61 (1 H, d, J=8.3 Hz), 7.38 (1 H, d, J=1.9 Hz), 7.29 (1 H, dd, J=8.0, 2.0 Hz), 7.24 (1 H, dd, J=7.7, 2.7) 6.82 (1 H, dd, J=3.0, 8.1 Hz), 6.69 (1 H, m), 3.80 (1 H, br s) 3.68-3.62 (2 H, m), 3.40-3.34 (2 H, m), 2.22-2.16 (2 H, m), 1.87-1.81 (2 H, m), 1.45 (9 H, s).

Sources & evidence

ORD record
ord-423543ce74854feb93f943c8e2fe20aa
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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