Trifluoroacetic acid → HCID 178486737, compound

HRID 890969Notes

Reaction equation

HRID 890969 reaction equation
C([O:5][C:6]([CH2:8][NH:9][C:10]([NH:33][C:34]1[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][C:35]=1[CH3:41])=[N:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH:26]3[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:6]([CH2:8][NH:9][C:10]([NH:33][C:34]1[C:35]([CH3:41])=[CH:36][CH:37]=[CH:38][C:39]=1[CH3:40])=[N:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:24][CH2:25][CH:26]3[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]3)=[C:19]([O:22][CH3:23])[CH:20]=2)[N:15]=[CH:14][N:13]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178486734HCID 178486734, compound

Product 1

HCID 178486737HCID 178486737, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(tert-butoxycarbonylmethyl)-N′-(2,6-dimethylphenyl)-N″-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]guanidine (0.09 g), trifluoroacetic acid (1 ml) and methylene chloride (1 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixture of methylene chloride and a 2M solution of ammonia gas in methanol as eluent. There was thus obtained the title compound in 67% yield: NMR Spectrum: (DMSOd6, 100° C.) 1.2–1.5 (m, 3H), 1.7–1.9 (m, 2H), 2.0–2.1 (m, 2H), 2.14 (s, 3H), 2.19 (s, 6H), 2.84 (d, 2H), 3.82 (s, 3H), 3.95–4.05 (m, 4H), 7.08 (s, 1H), 7.17 (s, 3H), 7.71 (s, 1H), 8.43 (s, 1H); Mass Spectrum: M+H+ 507.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. temperatureincreasingly polar
  4. additionmixture of methylene chloride

Sources & evidence

ORD record
ord-6f845cde990742d2bbba03c08f4b124b
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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