Pyridine → HCID 59843048, compound

HRID 1878773Notes

Reaction equation

HRID 1878773 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7]1.[C:22](Cl)(=O)[O:23]C1C=CC([N+]([O-])=O)=CC=1.N1C=CC=CC=1.[O:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][CH2:49][NH2:50])[CH2:43][CH2:42]1>C(Cl)Cl.CCOC(C)=O>[O:41]1[CH2:46][CH2:45][N:44]([CH2:47][CH2:48][CH2:49][NH:50][C:22]([NH:1][C:2]2[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][N:6]3[C:11](=[O:12])[CH:10]=[CH:9][C:8]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[N:7]3)[CH:3]=2)=[O:23])[CH2:43][CH2:42]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 61055N-(3-Aminopropyl)morpholineHCID 821294-Nitrophenyl chloroformateHCID 59843053HCID 59843053, compound

Product 1

HCID 59843048HCID 59843048, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3-aminobenzyl)-6-phenylpyridazin-3(2H)-one (280 mg, 1010 μmol) and 4-nitrophenyl carbonochloridate (215 mg, 1067 μmol) in CH2Cl2 (5 mL) was added pyridine (82 μl, 1010 μmol). The resulting mixture was stirred at rt overnight. A solution of 3-morpholinopropan-1-amine (170 mg, 1179 μmol) in CH2Cl2 (3 mL) was added to the mixture, resulting in a yellow solution. After 1 h, the solution was diluted with EtOAc (30 mL) and was washed with NaOH (1 N, 10 mL, 3×). The organic layer was further washed with H2O (10 mL), NaHCO3 (satd., 10 mL), dried over Na2SO4 and concentrated. The yellow film was triturated with hexane-EtOAc (2:1). The oil was washed with ether, acetone in ether (10%), and pumped to a yellow foam (>110 mg). LCMS (ESI pos. ion): calc'd for C25H29N5O3: 447.5; found: 448.3 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.63-1.71 (m, 2 H) 2.32-2.43 (m, 6 H) 3.26-3.36 (m, 2 H) 3.52-3.59 (m, 4 H) 5.36 (s, 2 H) 5.51 (br. s., 1 H) 6.71 (br. s., 1 H) 7.01 (d, J=10.04 Hz, 1 H) 7.19 (d, J=7.53 Hz, 1 H) 7.24-7.31 (m, 1 H) 7.32 (s, 1 H) 7.36 (d, J=8.03 Hz, 1 H) 7.40-7.50 (m, 3 H) 7.67 (d, J=9.54 Hz, 1 H) 7.78 (d, J=7.53 Hz, 2 H).

Workup

  1. customresulting in a yellow solution
  2. waitAfter 1 h
  3. washwas washed with NaOH (1 N, 10 mL, 3×)
  4. washThe organic layer was further washed with H2O (10 mL), NaHCO3 (satd., 10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe yellow film was triturated with hexane-EtOAc (2:1)
  8. washThe oil was washed with ether, acetone in ether (10%)

Sources & evidence

ORD record
ord-7a0dbeff091b49309ac118c6490dc136
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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