Acetonitrile → HCID 178486865, compound

HRID 890973Notes

Reaction equation

HRID 890973 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][N:9]([CH3:38])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([NH:29][C:30]1[C:35]([CH3:36])=[CH:34][CH:33]=[CH:32][C:31]=1[CH3:37])=[N:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([OH:28])=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[CH:18][N:17]=1.C(N(CC)C(C)C)(C)C.C(#N)C>CCCCCC.CO>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][C:22]=1[O:28][CH3:1])[N:19]=[CH:18][N:17]=[C:16]2[NH:15][C:14]([NH:13][CH2:12][CH2:11][CH2:10][N:9]([CH3:8])[CH3:38])=[N:29][C:30]1[C:31]([CH3:37])=[CH:32][CH:33]=[CH:34][C:35]=1[CH3:36]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 178486726HCID 178486726, compound

Product 1

HCID 178486865HCID 178486865, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

An aliquot (0.15 ml) of a 2M solution of trimethylsilyldiazomethane in hexane was added to a mixture of N-(3-dimethylaminopropyl)-N′-(2,6-dimethylphenyl)-N″-(7-hydroxy-6-methoxyquinazolin-4-yl)guanidine (0.1 g), N,N-diisopropylethylamine (0.06 ml), acetonitrile (1.8 ml) and methanol (0.2 ml). The resultant reaction mixture was stirred at ambient temperature for 16 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a 2M solution of ammonia gas in methanol as eluent. There was obtained the title compound (0.059 g); NMR Spectrum: (DMSOd6, 100° C.) 1.78 (m, 2H), 2.06 (s, 6H), 2.3 (s, 6H), 2.38 (t, 2H), 3.6 (q, 2H), 3.81 (s, 3H), 3.93 (s, 3H), 7.11 (s, 1H), 7.2 (s, 3H), 7.66 (s, 1H), 8.47 (s, 1H), 10.9 (br s, 1H); Mass Spectrum: M+H+ 473.

Workup

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

Sources & evidence

ORD record
ord-49db70496fbc4de890401ca230dbeefb
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

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