Thionyl Chloride → HCID 68011885, compound

HRID 920961Notes

Reaction equation

HRID 920961 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[NH:11][N:10]=2)=[CH:4][C:3]=1[C:20]([N:22]1[CH2:27][CH2:26][N:25]2[C:28]([C:33]([F:36])([F:35])[F:34])=[N:29][C:30]([CH2:31]O)=[C:24]2[CH2:23]1)=[O:21].S(Cl)([Cl:39])=O>>[Cl:39][CH2:31][C:30]1[N:29]=[C:28]([C:33]([F:36])([F:35])[F:34])[N:25]2[CH2:26][CH2:27][N:22]([C:20]([C:3]3[CH:4]=[C:5]([CH2:8][C:9]4[C:18]5[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=5)[C:12](=[O:19])[NH:11][N:10]=4)[CH:6]=[CH:7][C:2]=3[F:1])=[O:21])[CH2:23][C:24]=12

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 56833305HCID 56833305, compound

Product 1

HCID 68011885HCID 68011885, compoundYield 96.6%

Procedure

4-[[4-Fluoro-3-[1-(hydroxymethyl)-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carbonyl]phenyl]methyl]-2H-phthalazin-1-one 6 (200 mg, 0.40 mmol) was dissolved in 5 mL of thionyl chloride. The reaction mixture was heated to reflux for 4 hours. The reaction mixture was concentrated under reduced pressure, added with 10 mL of H2O, extracted with dichloromethane (10 mL×3). The organic phase was combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 4-[[3-[1-(chloromethyl)-3-(trifluoromethyl)-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carbonyl]-4-fluoro-phenyl]methyl]-2H-phthalazin-1-one 9a (200 mg, yield 96.6%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionadded with 10 mL of H2O
  5. extractionextracted with dichloromethane (10 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-305144fa5dad44659c0dc5e0628574c5
Source dataset
uspto-grants-2016_03
Patent number
US09273052B2

Reaction notes

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