Formamide → HCID 136386010, compound

HRID 902413Notes

Reaction equation

HRID 902413 reaction equation
C(O[C:6]([C:8]1[C:17]([NH2:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([O:28][CH3:29])=[C:13]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[CH:14]=2)[CH:9]=1)=[O:7])(C)(C)C.[CH:30]([NH2:32])=O>C(Cl)Cl.CO>[CH3:29][O:28][C:12]1[C:13]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:14][C:15]2[CH:16]=[C:17]3[C:8]([C:6](=[O:7])[NH:32][CH:30]=[N:18]3)=[CH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 2

HCID 713FormamideHCID 120627393-Amino-7-methoxy-6-(2-morpholin-4-yl-ethoxy)-naphthalene-2-carboxylic acid tert-butyl ester

Product 1

HCID 136386010HCID 136386010, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
178 °C

Procedure

A mixture of 3.5 g (8.6 mmol) of 3-amino-7-methoxy-6-(2-morpholin-4-yl-ethoxy)-naphthalene-2-carboxylic acid tert-butyl ester and 60 ml of formamide is heated at 178° C. for 2 hours, then cooled. To this is added 4:1 methylene chloride/methanol. The resulting solution is washed several times with brine, dried over anhydrous sodium sulfate and evaporated to yield an oil. The oil is purified by silica gel chromatography, utilizing a gradient of 99:1 to 88:12 methylene chloride/methanol to give sticky solid, which is triturated with ethyl acetate to yield 1.5 g of 7-methoxy-8-(2-morpholin-4-yl-ethoxy)-3H-benzo[g]quinazolin-4-one as a tan solid, mp 230-232° C.

Workup

  1. temperaturecooled
  2. washThe resulting solution is washed several times with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto yield an oil
  6. customThe oil is purified by silica gel chromatography
  7. customto give sticky solid, which
  8. customis triturated with ethyl acetate

Sources & evidence

ORD record
ord-68a88866bb6148318731f2d566f3ccb5
Source dataset
uspto-grants-2008_04
Patent number
US07365197B2

Reaction notes

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