Trifluoroacetic acid → HCID 178486732, compound

HRID 890971Notes

Reaction equation

HRID 890971 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]([NH:35][C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:43])=[N:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][NH:11][C:12]([NH:35][C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[CH3:43])=[N:13][C:14]1[C:23]2[C:18](=[CH:19][C:20]([O:26][CH2:27][CH:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)=[C:21]([O:24][CH3:25])[CH:22]=2)[N:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178486731HCID 178486731, compound

Product 1

HCID 178486732HCID 178486732, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-tert-butoxycarbonylaminoethyl)-N′-(2,6-dimethylphenyl)-N″-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]guanidine (0.31 g), trifluoroacetic acid (1 ml) and methylene chloride (1 ml), was stirred at ambient temperature for 20 minutes. The reaction mixture was evaporated and the residue was dissolved in water (4 ml) and the solution was basified to pH10 by the addition of 10N aqueous potassium hydroxide solution. The mixture was extracted with a 19:1 mixture of methylene chloride and methanol. The organic extract was dried over magnesium sulphate and evaporated. There was thus obtained the title compound (0.16 g); NMR Spectrum: (DMSOd6) 1.2–1.4 (m, 2H), 1.65–1.94 (m, 5H),2.12 (s, 3H), 2.21 (s, 6H), 2.7–2.9 (m, 4H), 3.22 (br s, 3H), 3.4–3.8 (m, 4H), 3.91 (d, 2H), 7.0 (s, 1H), 7.13 (s, 3H), 8.4 (s, 1H); Mass Spectrum: M+H+ 492.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in water (4 ml)
  3. additionthe solution was basified to pH10 by the addition of 10N aqueous potassium hydroxide solution
  4. extractionThe mixture was extracted with a 19:1 mixture of methylene chloride and methanol
  5. extractionThe organic extract
  6. dry with materialwas dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-2b393a6587f7495c86cd42c285e2f740
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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