Triethylamine → HCID 67316418, compound

HRID 1012963Notes

Reaction equation

HRID 1012963 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N:18]3[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:42]=[CH:41][C:37]([C:38]([Cl:40])=[O:39])=[CH:36][CH:35]=1>ClCCl>[ClH:40].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([N:18]3[CH2:23][CH2:22][CH:21]([NH:24][C:38](=[O:39])[C:37]4[CH:41]=[CH:42][C:34]([C:33]([F:32])([F:43])[F:44])=[CH:35][CH:36]=4)[CH2:20][CH2:19]3)=[N:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 66971042HCID 66971042, compound

Product 1

HCID 67316418HCID 67316418, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-(4-(4-fluorophenyl)phthalazin-1-yl)piperidin-4-amine (110 mg, 0.34 mmol), triethylamine (0.14 mL, 1.02 mmol) and dichloromethane (2 mL) at room temperature. Add 4-(trifluoromethyl)-benzoyl chloride (85 mg, 0.41 mmol) to the mixture and stir at room temperature overnight. Concentrate the reaction mixture and purify the resulting residue by flash chromatography (20:5:1. hexane:ethyl acetate: 2 M ammonia in methanol). Add 1 N HCl in diethyl ether to a solution of the isolated product in dichloromethane/methanol and remove the solvents under a stream of nitrogen gas to yield the title compound as a solid (57 mg, 32%). ES/MS m/z 495.2 (M+1).

Workup

  1. customat room temperature
  2. concentrationConcentrate the reaction mixture
  3. custompurify the resulting residue by flash chromatography (20:5:1. hexane:ethyl acetate: 2 M ammonia in methanol)
  4. additionAdd 1 N HCl in diethyl ether to a solution of the isolated product in dichloromethane/methanol
  5. customremove the solvents under a stream of nitrogen gas

Sources & evidence

ORD record
ord-6e7fde807e694ecc8605ac9997d95a96
Source dataset
uspto-grants-2011_07
Patent number
US07981892B2

Reaction notes

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