HCID 86675176, compound → HCID 86675175, compound

HRID 1502852Notes

Reaction equation

HRID 1502852 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.C(O)(=O)C>[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 acetic acid (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 ethyl acetate and the separated ethyl acetate layer dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound. The crude compound was triturated with diethyl ether-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 ethyl acetate
  4. dry with materialthe separated ethyl acetate layer dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude compound
  7. customThe crude compound was triturated with diethyl ether-pentane mixture

Sources & evidence

ORD record
ord-c417a113b7634928a807f0f420de5dc5
Source dataset
uspto-grants-2015_12
Patent number
US09211280B2

Reaction notes

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