Triethylamine → 2-[4-(4-Methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-1-morpholin-4-yl-ethanone

HRID 646941Notes

Reaction equation

HRID 646941 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[CH2:33][C:34]([N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)=[O:35]>C(Cl)Cl>[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][N:22]([CH2:33][C:34]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[O:35])[CH2:21][CH2:20]3)[N:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 686831104-Methyl-3'-nitro-6'-piperazin-1-yl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl dihydrobromide

Product 1

HCID 586385422-[4-(4-Methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-1-morpholin-4-yl-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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), 0.10 g, 0.21 mmol) in CH2Cl2 (5 mL) was treated with Et3N (0.10 mL, 0.75 mmol) and 2-chloro-1-morpholin-4-yl-ethanone (as prepared in the previous step, 39 mg, 0.24 mmol). The reaction stirred at room temperature for 18.5 h. The reaction was diluted with CH2Cl2 and washed with water. The aqueous layer was further extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.11 g, 117%, some salt remains) as a yellow solid, which was used directly in the next step without further purification. 1H-NMR (CDCl3; 400 MHz): δ 8.19 (d, 1H, J=9.2 Hz), 6.02 (d, 1H, J=9.2 Hz), 3.76-3.67 (m, 8H), 3.26 (br s, 2H), 3.14-3.07 (m, 2H), 3.03-2.93 (m, 2H), 2.63 (br s, 4H), 1.74-1.65 (m, 2H), 1.65-1.58 (m, 1H), 1.45-1.39 (m, 3H), 1.37-1.24 (m, 3H), 0.97 (d, 3H, J=6.4 Hz). LC-MS (ESI, m/z): Calcd. for C21H32N6O4, 433.2 (M+H), found 433.1.

Workup

  1. customas prepared in the previous step, 39 mg, 0.24 mmol)
  2. washwashed with water
  3. extractionThe aqueous layer was further extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa49cc484ab8434bb8686a2092dfb7d2
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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