Diisopropylethylamine → HCID 25054678, compound

HRID 1400089Notes

Reaction equation

HRID 1400089 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:6]=[N:5][C:4]=1[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[F:20][C:21]([F:31])([F:30])[C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.C(N(C(C)C)CC)(C)C>C(#N)C.Cl.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[N:6]=[N:5][C:4]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([C:21]([F:20])([F:30])[F:31])[CH:23]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzeneHCID 59233384HCID 59233384, compound

Product 1

HCID 25054678HCID 25054678, compoundYield 109.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of (4-methoxy-6-trifluoromethyl-pyridazin-3-yl)-piperidin-4-yl-amine (D8) (0.10 g, 0.36 mmol), 3-trifluoromethyl-benzyl bromide (0.060 ml, 0.29 mmol) and diisopropylethylamine (0.138 ml, 0.79 mmol) in acetonitrile (2 ml) was stirred at room temperature for 16 h. After this period, the solvent was evaporated in vacuo and the crude product purified by short open column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane). The desired fractions were collected and evaporated in vacuo. The product thus obtained was dissolved in a solution 2M of hydrochloric acid in diethyl ether to yield the corresponding hydrochloride salt E4 (0.138 g, 88%) as a solid. C19H20F6N4O.HCl free base requires 434; Found 435 (MH+). Rt (Method 1): 4.73 min.

Workup

  1. waitAfter this period
  2. customthe solvent was evaporated in vacuo
  3. customthe crude product purified by short open column chromatography (silica gel; 3% ammonia in methanol (7M)/dichloromethane)
  4. customThe desired fractions were collected
  5. customevaporated in vacuo
  6. customThe product thus obtained

Sources & evidence

ORD record
ord-7c270af2c9c94b389ea2362407568e99
Source dataset
uspto-grants-2014_12
Patent number
US08906921B2

Reaction notes

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