Chloroacetyl chloride → 2-Chloro-1-[4-(4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-ethanone

HRID 646943Notes

Reaction equation

Br.Br.[CH3:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:11]=2)[CH2:6][CH2:5]1.CCN(CC)CC.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[Cl:32][CH2:33][C:34]([N:22]1[CH2:23][CH2:24][N:19]([C:12]2[N:11]=[C:10]([N:7]3[CH2:8][CH2:9][CH:4]([CH3:3])[CH2:5][CH2:6]3)[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=2)[CH2:20][CH2:21]1)=[O:35]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-methyl-3′-nitro-6′-piperazin-1-yl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl dihydrobromide (as prepared in Example 67, step (c), 0.28 g, 0.60 mmol) in CH2Cl2 (6 mL) was treated with Et3N (0.27 mL, 1.9 mmol) and cooled to 0° C. The mixture was treated with chloroacetyl chloride (53 μL, 0.66 mmol) as a solution in CH2Cl2 (2 mL) and stirred at 0° C. for 15 min then at room temperature for 30 min. The reaction was diluted with CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (0.18 g, 80%) as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.21 (d, 1H, J=9.2 Hz), 6.03 (d, 1H, J=9.2 Hz), 4.11 (s, 2H), 3.84-3.76 (m, 4H), 3.76-3.61 (m, 4H), 3.13-3.05 (m, 1H), 3.04-2.92 (m, 2H), 1.7-1.66 (m, 2H), 1.45-1.38 (m, 2H), 1.38-1.25 (m, 2H), 0.98 (d, 3H, J=6.4 Hz). LC-MS (ESI, m/z): Calcd. for C17H24ClN5O3, 382.1 (M+H), found 382.1.

Workup

waitat room temperature for 30 min
washwashed with water
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6dfdfc6b26b048aa819b87cd5ac58b90
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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