Ethanol → HCID 178486729, compound

HRID 890980Notes

Reaction equation

HRID 890980 reaction equation
[CH3:1][N:2]([CH3:44])[CH2:3][CH2:4][NH:5][C:6]([NH:35][C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:43])=[N:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][CH:22]3[CH2:27][O:26][CH2:25][CH2:24][N:23]3CC3C=CC=CC=3)=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][N:9]=1.FC(F)(F)C(O)=O.C(O)C.[H][H]>[Pd].C(Cl)Cl>[CH3:44][N:2]([CH3:1])[CH2:3][CH2:4][NH:5][C:6]([NH:35][C:36]1[C:37]([CH3:43])=[CH:38][CH:39]=[CH:40][C:41]=1[CH3:42])=[N:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH2:21][CH:22]3[CH2:27][O:26][CH2:25][CH2:24][NH:23]3)=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 178418361HCID 178418361, compoundHCID 178486730HCID 178486730, compound

Product 1

HCID 178486729HCID 178486729, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-dimethylaminoethyl)-N′-(2,6-dimethylphenyl)-N″-[7-(N-benzylmorpholin-3-ylmethoxy)-6-methoxyquinazolin-4-yl]guanidine (0.1 g), trifluoroacetic acid (0.091 ml), 10% palladium on carbon catalyst (0.03 g) and ethanol (12 ml) was stirred under an atmosphere pressure of hydrogen for 18 hours. The reaction was filtered and the filtrate was evaporated. The resulting gum was triturated under diethyl ether to give a solid which was dissolved in methylene chloride. The solution was washed with cooled 1N aqueous sodium hydroxide solution and with water. The organic solution was dried over magnesium sulphate and evaporated. There was thus obtained the title compound (0.069 g): NMR Spectrum: (CDCl3) 2.1 (s, 6H), 2.26 (s, 6H), 2.39 (m, 2H), 2.9 (m, 2H), 3.36 (m, 2H), 3.55 (m, 3H), 3.78 (d, 2H), 3.80–4.08 (m, 5H), 4.79 (s, 1H), 7.1 (s, 4H), 7.85 (s, 1H), 8.47 (s, 1H), 12.5 (s, 1H); Mass Spectrum: M+H+ 508.

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate was evaporated
  3. customThe resulting gum was triturated under diethyl ether
  4. customto give a solid which
  5. washThe solution was washed
  6. temperaturewith cooled 1N aqueous sodium hydroxide solution
  7. dry with materialThe organic solution was dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-da58179a0fb24baa95814aa2b136c809
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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