HCID 58075657, compound → HCID 58075447, compound

HRID 475919Notes

Reaction equation

HRID 475919 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH3:13])[C:9]2[CH:8]=[CH:7][CH2:6][C:5]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([OH:14])[C:4]=2[N:3]=1.[Cl:21][C:22]1[N:23]=[CH:24][N:25]([C:27]2[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][C:28]=2[O:34][CH3:35])[CH:26]=1>O1CCOCC1.C(O)(=O)C>[Cl:21][C:22]1[N:23]=[CH:24][N:25]([C:27]2[CH:33]=[CH:32][C:30]([NH:31][C:2]3[N:11]=[C:10]([NH:12][CH3:13])[C:9]4[CH:8]=[CH:7][CH2:6][C:5]([C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)([OH:14])[C:4]=4[N:3]=3)=[CH:29][C:28]=2[O:34][CH3:35])[CH:26]=1

Participants

5

Reactant 2

HCID 58075657HCID 58075657, compoundHCID 580757574-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline

Product 1

HCID 58075447HCID 58075447, compoundYield 43.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-chloro-4-(methylamino)-8-phenyl-7,8-dihydroquinazolin-8-ol (25 mg) and 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyaniline (29 mg) in dioxane (0.2 mL) and acetic acid (0.2 mL) was heated at 85° C. for 4 h. THF was removed in vacuo, and the residue was purified by reverse phase preparative to give the title compound (as its TFA salt) as an oil (18 mg). LC-MS (M+H)+=475.26. 1H NMR (TFA salt, 500 MHz, CD3OD) δ ppm 7.2-7.9 (m), 6.56 (1H, m), 6.18 (1H, m), 3.94 (3H, s), 3.20 (3H, s), 3.10 (2H, m).

Workup

  1. customTHF was removed in vacuo
  2. customthe residue was purified by reverse phase preparative

Sources & evidence

ORD record
ord-9cf9a64b39d84a9192d5fdf34ab329a3
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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