HCID 54427620, compound → HCID 19043379, compound

HRID 1079476Notes

Reaction equation

HRID 1079476 reaction equation
[O:1]=[C:2]1[N:8]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:4](=[O:25])[C:3]1=[N:26]NC1C=CC=CC=1>C(O)(=O)C.O.[Zn]>[NH2:26][CH:3]1[C:2](=[O:1])[N:8]([CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]2[CH:14]=[CH:15][CH:16]=[CH:17][C:6]=2[N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C:4]1=[O:25]

Participants

5

Reactant 1

HCID 54427620HCID 54427620, compound

Product 1

HCID 19043379HCID 19043379, compoundYield 60.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of the intermediate 2 (5.8 g) in glacial acetic acid (50 ml) was added, dropwise, to a suspension of zinc dust (6.37 g) in glacial acetic acid (20 ml) cooled to 0°. The mixture was stirred at 23° for 3 h, then diluted with water (200 ml) and decanted from zinc. Solid sodium carbonate was added until pH=9 and the mixture extracted with ethyl acetate (2×300 ml). The combined organic extracts were washed with brine (300 ml), dried and concentrated in vacuo to an oil which was purified by flash chromatography (eluting in gradient from CH-EA 2:1 to EA) to give the title compound as a white foam (2.8 g). M.p. 125°-6°. T.l.c. DCM-methanol (30:1), Rf 0.38.

Workup

  1. temperaturecooled to 0°
  2. customdecanted from zinc
  3. additionSolid sodium carbonate was added until pH=9
  4. extractionthe mixture extracted with ethyl acetate (2×300 ml)
  5. washThe combined organic extracts were washed with brine (300 ml)
  6. customdried
  7. concentrationconcentrated in vacuo to an oil which
  8. customwas purified by flash chromatography (eluting in gradient from CH-EA 2:1 to EA)

Sources & evidence

ORD record
ord-e1ac0e75c42e4de7b87425101b6f3c9b
Source dataset
uspto-grants-1996_12
Patent number
US05580895

Reaction notes

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