Hydrochloric Acid → HCID 68616146, compound

HRID 2233755Notes

Reaction equation

HRID 2233755 reaction equation
[CH3:1][N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([C:28]1[CH:49]=[CH:48][C:31]([O:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([F:42])[CH:40]=3)[N:35]([CH2:43][C:44]([OH:46])=[O:45])[C:34]=2[CH3:47])=[CH:30][CH:29]=1)([OH:27])=O.[CH3:50]CN(C(C)C)C(C)C.CN.Cl>CN1C(=O)CCC1.C1COCC1>[F:42][C:39]1[CH:40]=[C:41]2[C:36](=[CH:37][CH:38]=1)[N:35]([CH2:43][C:44]([O:46][CH3:50])=[O:45])[C:34]([CH3:47])=[C:33]2[O:32][C:31]1[CH:30]=[CH:29][C:28]([C:25]([NH:2][CH3:1])=[O:27])=[CH:49][CH:48]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 116026043-(4-Carboxyphenoxy)-5-fluoro-2-methyl-1h-indole-1-acetic acid

Product 1

HCID 68616146HCID 68616146, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

HATU (294 mg) was added to a solution of the product from Example 9 (208 mg) and Hunig's base (0.3 ml) in NMP (1.2 ml). After 10 min a solution of methylamine in THF (0.4 ml, 2M) was added and stirred for 20 h. 2M HCl (1 ml) was added and the mixture was extracted with ethyl acetate. The organic extracts were dried (MgSO4), evaporated, re-dissolved in methanol and treated with a solution of trimethylsilyldiazomethan (1 ml, 2M in ether). Evaporation and purification by chromatography (silica, petrol—acetone as eluent) gave the sub-title compound (177 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. customevaporated
  4. dissolutionre-dissolved in methanol
  5. additiontreated with a solution of trimethylsilyldiazomethan (1 ml, 2M in ether)
  6. customEvaporation and purification by chromatography (silica, petrol—acetone as eluent)

Sources & evidence

ORD record
ord-4ddaa1e00038467bb49d7458cd043b36
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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