Hydrochloric Acid → HCID 67374691, compound

HRID 2168757Notes

Reaction equation

HRID 2168757 reaction equation
[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:20][CH:21]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([O:18][CH3:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4].[CH:28]1(O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[ClH:68]>C1COCC1.C(Cl)Cl.CCOCC>[ClH:68].[ClH:68].[CH2:1]([C:5]1[N:6]=[N:7][C:8]([O:20][CH:21]2[CH2:22][CH2:23][N:24]([CH3:27])[CH2:25][CH2:26]2)=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:13]([O:18][CH3:19])[CH:12]=1)[CH2:2][CH2:3][CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7966CyclohexanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136386260HCID 136386260, compound

Product 1

HCID 67374691HCID 67374691, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-methoxy-phenol (1.0 mmol, 371 mg) in dry THF (3.0 mL) was added cyclohexanol (3.0 mmol, 317 μL) and triphenylphosphine (3.0 mmol, 787 mg). While sonicating, diisopropyl azodicarboxylate (3.0 mmol, 591 μL) was added. And the mixture was sonicated for another 1 hour then condensed. The residue was purified by silica gel chromatography (DCM to DCM+10% MeOH) to afford a colorless sticky solid, which was dissolved in DCM (5.0 mL), 2N HCl in ether (5.0 mL) was added, condensed, triturated with hexanes to provide the title compound (332 mg). LCMS: m/z 455 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.09 (1H, d), 6.98-7.03 (2H, m), 6.90-6.93 (1H, m), 5.45 (1H, bs), 4.30-4.38 (1H, m), 3.85 (3H, s), 3.10-3.37 (4H, m), 2.90-2.96 (2H, m), 2.79 (3H, s), 2.10-2.35 (4H, m), 1.96-2.03 (2H, m), 1.80-1.87 (2H, m), 1.31-1.63 (8H, m), 1.20-1.29 (2H, m), 0.80 (3H, t).

Workup

  1. customWhile sonicating
  2. customAnd the mixture was sonicated for another 1 hour
  3. customcondensed
  4. customThe residue was purified by silica gel chromatography (DCM to DCM+10% MeOH)
  5. customto afford a colorless sticky solid, which
  6. customcondensed
  7. customtriturated with hexanes

Sources & evidence

ORD record
ord-6ac3cef021174e10a75b04d918690465
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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