1,2-Dichloroethane → HCID 53629034, compound

HRID 244112Notes

Reaction equation

HRID 244112 reaction equation
[Cl:1][C:2]1[C:3]([CH:8]([C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:17]3)=[CH:12][CH:11]=2)[NH2:9])=[N:4][CH:5]=[CH:6][N:7]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[C:49]([N:59]1[CH2:64][CH2:63][CH:62]([CH2:65][C:66](O)=[O:67])[CH2:61][CH2:60]1)([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50]>C(Cl)Cl>[CH2:52]([O:51][C:49]([N:59]1[CH2:64][CH2:63][CH:62]([CH2:65][C:66](=[O:67])[NH:9][CH:8]([C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][C:16]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[N:17]3)=[CH:12][CH:11]=2)[CH2:61][CH2:60]1)=[O:50])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1502086N-Cbz-4-piperidineacetic acidHCID 51051365(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)methanamine

Product 1

HCID 53629034HCID 53629034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)-methanamine (120.00 mg, 0.35 mmol), EDC (100.64 mg, 0.53 mmol) and HOBt (47.29 mg, 0.35 mmol) were suspended in CH2Cl2 (2 mL) and charge with DIEA (122.00 μL, 0.70 mmol) followed by the addition of 1-N-Cbz-4-piperidineacetic acid (127.56 mg, 0.46 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was diluted with CH2Cl2 (10 mL) and washed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a 10 g Jones silica gel (wetted with 50% EtOAc/Hexane, dried loaded onto silica, and run with 60% EtOAc/Hexanes→70% EtOAc/Hexanes) affording the desired product; 1H NMR (400 MHz, CHLOROFORM-d) δ 8.56 (1H, d, J=2.47), 8.39 (1H, d, J=2.50), 8.23 (1H, d, J=4.77), 8.11 (2H, d, J=7.06), 7.85 (3H, dd, J=8.60, J=8.38), 7.74 (1H, s), 7.50 (3H, m), 7.32 (6H, m), 6.78 (1H, d, J=7.76), 5.10 (2H, s), 4.11 (2H, m), 2.75 (2H, m), 2.21 (2H, d, J=7.00), 2.01 (1H, m), 1.67 (2H, m), 1.15 (2H, d, J=8.921); MS (ES+): m/z 605.96/606.98/608.93 (100/40/15) [MH+]; HPLC: tR=3.33 min. (OpenLynx, nonpolar—5 min.).

Workup

  1. washwashed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by a 10 g Jones silica gel (wetted with 50% EtOAc/Hexane, dried loaded onto silica, and run with 60% EtOAc/Hexanes→70% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-5bb9bb654f89472b867b298fe6e419f2
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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