Dimethylformamide → HCID 57955319, compound

HRID 73678Notes

Reaction equation

HRID 73678 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[C:9]([CH2:12][O:13][CH3:14])=[C:10](Br)[N:6]2[N:5]=[CH:4][N:3]=1.[Li]CCCC.CN([CH:45]=[O:46])C>C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[C:17]([F:36])[CH:16]=3)[C:9]([CH2:12][O:13][CH3:14])=[C:10]([CH:45]=[O:46])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 57955300HCID 57955300, compoundHCID 178418339Butyllithium

Product 1

HCID 57955319HCID 57955319, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-77 °C

Procedure

To a solution of THF (35 mL) was added 1-{4-[4-amino-7-bromo-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-fluorophenyl}-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea (200 mg, 0.35 mmol). The solution was cooled to −77° C., and then 2.5 M n-BuLi in hexanes (0.70 mL, 1.75 mmol) was added. The reaction was stirred for 1 min and then DMF (0.16 mL, 2.1 mmol) was added. The solution was stirred for an additional 5 min, and the ice bath was removed. The reaction was allowed to warm to rt over the following 1 h. EtOAc was added to the solution followed by water. The solution was separated and the aqueous layer was back extracted with EtOAc. The combined organic fractions were dried (MgSO4), filtered, and evaporated yielding the title compound as crude material (216 mg, 119%). MS [M+H]+=521; LCMS RT=3.49.

Workup

  1. stirringThe solution was stirred for an additional 5 min
  2. customthe ice bath was removed
  3. temperatureto warm to rt over the following 1 h
  4. additionEtOAc was added to the solution
  5. customThe solution was separated
  6. extractionthe aqueous layer was back extracted with EtOAc
  7. dry with materialThe combined organic fractions were dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4d137f48da8e44e4aa322abbce2a8bb7
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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