Ammonia → HCID 178478360, compound

HRID 386152Notes

Reaction equation

HRID 386152 reaction equation
O=P(Cl)(Cl)Cl.[Cl:6][C:7]1[C:8]([CH:13]([NH:30][C:31]([CH:33]2[CH2:36][CH2:35][CH2:34]2)=O)[C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:21]3)=[CH:16][CH:15]=2)=[N:9][CH:10]=[CH:11][N:12]=1.N.CC(O)C>>[Cl:6][C:7]1[C:8]2[N:9]([CH:31]([CH:33]3[CH2:36][CH2:35][CH2:34]3)[NH:30][C:13]=2[C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][C:20]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[N:21]3)=[CH:16][CH:15]=2)[CH:10]=[CH:11][N:12]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 3776IsopropanolHCID 24813Phosphorus oxychlorideHCID 53629482N-[(3-chloro-2-pyrazinyl)(2-phenyl-7-quinolinyl)methyl]cyclobutanecarboxamide

Product 1

HCID 178478360HCID 178478360, compound

Conditions

Temperature
70 °C

Procedure

A mixture of POCl3 (5 mL, 8 g, 55 mmol) and cyclobutanecarboxylic acid [(3-chloropyrazin-2-yl)-(2-phenylquinolin-7-yl)methyl]-amide [275 mg, 0.583 mmol] is heated to 70° C. for 21.5 h. POCl3 is evaporated, a cold solution of NH3 in iPrOH (2M, 11 mL, 22 mmol) is added, the suspension is sonicated, the solid is filtered off and washed with iPrOH. The solid is suspended in CHCl3 and filtered, and the filtrate is concentrated to obtain the title compound as yellow solid. 1H NMR (CDCl3, 400 MHz) δ 2.04-2.15 (m, 1H), 2.15-2.28 (m, 1H), 2.50-2.60 (m, 2H), 2.64-2.76 (m, 2H), 3.89 (quint, J=8.4 Hz, 1H), 7.35 (d, J=4.8 Hz, 1H), 7.44-7.50 (m, 1H), 7.51-7.57 (m, 3H), 7.89-7.93 (m, 3H), 8.17-8.22 (m, 2H), 8.27 (dd, J=0.8, 8.8 Hz, 1H), 8.53 (d, J=0.8 Hz, 1H). MS (ES+): m/z 410.9/412.9 (100/39) [MH+]. HPLC: tR=3.7 min (MicromassZQ, nonpolar—5 min).

Workup

  1. customPOCl3 is evaporated
  2. customthe suspension is sonicated
  3. filtrationthe solid is filtered off
  4. washwashed with iPrOH
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-a05fe5dc0ddd405e8cce74fad54f8f67
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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