Ammonium Chloride → HCID 58229857, compound

HRID 221994Notes

Reaction equation

HRID 221994 reaction equation
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]([F:49])([F:48])[C:9]([NH:11][C:12]1([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:32]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:31][C:30]4[C:29]5=[N:39][N:40]=[C:41]([C:42]6[N:47]=[CH:46][CH:45]=[CH:44][N:43]=6)[N:28]5[CH:27]=[CH:26][C:25]=4[N:24]=3)=[CH:19][CH:18]=2)[CH2:15][C:14](=O)[CH2:13]1)=[O:10].[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[F:49][C:8]([F:48])([F:7])[C:9]([NH:11][C:12]1([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:32]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:31][C:30]4[C:29]5=[N:39][N:40]=[C:41]([C:42]6[N:43]=[CH:44][CH:45]=[CH:46][N:47]=6)[N:28]5[CH:27]=[CH:26][C:25]=4[N:24]=3)=[CH:21][CH:22]=2)[CH2:13][C:14](=[CH2:1])[CH2:15]1)=[O:10]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 582298532,2,2-trifluoro-N-(3-oxo-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide

Product 1

HCID 58229857HCID 58229857, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
30 °C

Procedure

A mixture of methyl(triphenyl)phosphonium bromide (111 mg, 0.311 mmol) and potassium tert-butoxide (35 mg, 0.311 mmol) in 1,4-dioxane (2 mL) was stirred at 30° C. for 30 minutes. 2,2,2-trifluoro-N-(3-oxo-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-2) (60 mg, 0.104 mmol) in 1,4-dioxane (2 mL) was added, and the mixture was stirred at room temperature for 15 hours. To the mixture was added NH4Cl, extracted with EtOAc, washed with water and brine, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. The residue was purified by column chromatography eluting with 0-10% methanol in CHCl3 to give 2,2,2-trifluoro-N-(3-methylene-1-{-4-[9-phenyl-3-(2-pyrimidinyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclobutyl)acetamide (4-11) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 hours
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography
  8. washeluting with 0-10% methanol in CHCl3

Sources & evidence

ORD record
ord-732ed131a93a4cf2a958f01b3a9ba23f
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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