Triethylamine → HCID 66971277, compound

HRID 1012965Notes

Reaction equation

HRID 1012965 reaction equation
Cl.Cl.[CH3:3][NH:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)=[N:13][N:12]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.[F:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([Cl:43])=[O:42])=[C:39]([C:46]([F:49])([F:48])[F:47])[CH:38]=1>ClCCl>[ClH:43].[C:25]([C:24]1[CH:27]=[CH:28][C:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:11]([N:8]3[CH2:7][CH2:6][CH:5]([N:4]([CH3:3])[C:41](=[O:42])[C:40]4[CH:44]=[CH:45][C:37]([F:36])=[CH:38][C:39]=4[C:46]([F:49])([F:48])[F:47])[CH2:10][CH2:9]3)=[N:12][N:13]=2)=[CH:22][CH:23]=1)#[N:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6056804-Fluoro-2-(trifluoromethyl)benzoyl chlorideHCID 66971335HCID 66971335, compound

Product 1

HCID 66971277HCID 66971277, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Charge a 4 mL reaction vial with 4-(4-(4-(methylamino)piperidine -1-yl)phthalazin -1-yl)benzonitrile dihydrochloride (44.7 mg, 0.107 mmol), dichloromethane (1 mL), and triethylamine (0.0598 mL, 0.429 mmol). Flush the reaction vial with nitrogen and add 4-fluoro-2-(trifluoromethyl)benzoyl chloride (033 g. 0.14 mmol). Cap the vial and allow the reaction to stir at room temperature overnight. Evaporate to a residue and purify using silica gel chromatography (40:60, ethyl acetate:hexane, then ethyl acetate). Add 1 N HCl in diethyl ether to a solution of the isolated product in dichloromethane/methanol and remove the solvents by placing under a stream of nitrogen gas. Dry in a vacuum oven at 50° C. to obtain the title compound (36.0 mg. 59%). ES/MS m/z 533.8 (M+1).

Workup

  1. additionCharge
  2. customFlush
  3. customthe reaction vial with nitrogen
  4. customCap the vial and
  5. customthe reaction
  6. customEvaporate to a residue
  7. custompurify
  8. additionAdd 1 N HCl in diethyl ether to a solution of the isolated product in dichloromethane/methanol
  9. customremove the solvents
  10. customDry in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-3269dd7e3a734705b1afdefcb2e50a8f
Source dataset
uspto-grants-2011_07
Patent number
US07981892B2

Reaction notes

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