Triethylamine → HCID 68743553, compound

HRID 1714762Notes

Reaction equation

HRID 1714762 reaction equation
[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7](C(O)=O)=[CH:8][CH:9]=2)[N:4]=[C:3]1[S:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:22][CH2:21]1.C([N:38](CC)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>C(O)(C)(C)C>[NH2:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][C:7]([NH2:38])=[CH:8][CH:9]=2)[N:4]=[C:3]1[S:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 23155812HCID 23155812, compound

Product 1

HCID 68743553HCID 68743553, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In 10 ml of tert-butanol, 250 mg of 3-amino-4-oxo-2-[3-(4-quinolin-2-ylpiperazin-1-yl)propylthio]-3,4-dihydroquinazolin-7-carboxylic acid as synthesized in Example 1-57 was dissolved, to which 52 mg of triethylamine, and further 147 mg of DPPA, were added by the order stated. This mixture was heated under reflux for an overnight. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=50:1). The purified product was added to 8 ml of 4N hydrochloric acid-dioxane solution, stirred for an hour, and an excessive amount of triethylamine was added. Distilling the solvent off under reduced pressure, the residue was purified on silica gel column chromatography (chloroform:methanol=50:1) to provide 20 mg (8%) of 3,7-diamino-2-[3-(4-quinolin-2-ylpiperazin-1-yl)propylthio]-3H-quinazolin-4-one.

Workup

  1. additionwere added by the order
  2. temperatureThis mixture was heated
  3. temperatureunder reflux for an overnight
  4. distillationDistilling the solvent off under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)
  6. additionThe purified product was added to 8 ml of 4N hydrochloric acid-dioxane solution
  7. additionan excessive amount of triethylamine was added
  8. distillationDistilling the solvent off under reduced pressure
  9. customthe residue was purified on silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-980eeffbd9574f5e9d8501eed57519bc
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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