HCID 86675176, compound → HCID 86675175, compound

HRID 587704Notes

Reaction equation

HRID 587704 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]1[N:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:16]=[CH:17]/[CH:18]([C:23]3[CH:28]=[C:27]([Cl:29])[C:26]([F:30])=[C:25]([Cl:31])[CH:24]=3)[C:19]([F:22])([F:21])[F:20])[CH:12]=2)[C:7]1=[O:32])C>Cl.CC(O)=O>[Cl:31][C:25]1[CH:24]=[C:23]([CH:18]([C:19]([F:21])([F:22])[F:20])/[CH:17]=[CH:16]/[C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:32])[N:6]([CH2:5][C:4]([OH:33])=[O:3])[N:15]=[CH:14]3)[CH:28]=[C:27]([Cl:29])[C:26]=1[F:30]

Participants

4

Reactant 1

HCID 86675176HCID 86675176, compound

Product 1

HCID 86675175HCID 86675175, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of (E)-ethyl-2-(6-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1-oxophthalazin-2(1H)-yl)acetate (0.04 g, 0.07 mmol) in HCl (0.5 mL) and AcOH (0.5 mL) was heated to 100° C. for 3 h. The solvent was removed under reduced pressure and the residue diluted with water. The aqueous layer was extracted with EtOAc and the separated EtOAc layer dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound. The crude compound was triturated with Et2O-pentane mixture to afford the title compound as a brown solid (0.03 g): 1H NMR (400 MHz, DMSO-d6) δ 13.0 (br s, 1H), 8.43 (m, 1H), 8.23 (d, J=8.1 Hz, 1H), 8.14 (m, 2H), 7.91 (m, 2H), 7.16 (dd, J=16.0, 8.0 Hz, 1H), 6.99 (d, J=16.0 Hz, 1H), 4.96 (m, 3H),; ESIMS m/z 473.0 ([M−H]−); IR (thin film) 1629, 1168, 817 cm−1.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe separated EtOAc layer dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude compound
  7. customThe crude compound was triturated with Et2O-pentane mixture

Sources & evidence

ORD record
ord-5a670693564b4f38809204f1adf4cfa8
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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