4-Methylmorpholine → 3-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(3,5-dimethylpiperidin-1-ylmethyl)phenyl]amide

HRID 735047Notes

Reaction equation

HRID 735047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([OH:18])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CN1CCOCC1.ClC(O[CH2:30][CH:31]([CH3:33])[CH3:32])=O.C[CH:35]1CC(C)C[CH:37]([NH:42][CH2:43][C:44]2[CH:49]=[CH:48][C:47]([NH2:50])=[CH:46][CH:45]=2)[CH2:36]1>C1COCC1>[CH3:32][CH:31]1[CH2:33][CH:36]([CH3:35])[CH2:37][N:42]([CH2:43][C:44]2[CH:45]=[CH:46][C:47]([NH:50][C:16](=[O:18])[C:15]#[C:14][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)=[CH:13][CH:12]=3)=[CH:48][CH:49]=2)[CH2:30]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 68816492(4'-Chlorobiphenyl-4-yl)propynoic acidHCID 688168134-[(3,5-Dimethylcyclohexylamino)methyl]phenylamine

Product 1

HCID 578458333-(4'-Chlorobiphenyl-4-yl)propynoic acid-[4-(3,5-dimethylpiperidin-1-ylmethyl)phenyl]amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.26 g (1 mmol) of (4′-chlorobiphenyl-4-yl)propynoic acid and 0.12 mL (1.1 mmol) of N-methylmorpholine in 20 mL of absolute THF is combined with 0.14 mL (1.1 mmol) of isobutyl chloroformate at −15° C. and stirred for ten minutes. Then 0.240 mg (1.1 mmol) of 4-[(3,5-dimethylcyclohexylamino)methyl]phenylamine dissolved in 7 mL of THF is added and the reaction mixture is stirred for 16 hours. The reaction mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol=90/10). Yield: 300 mg (66% of theory); melting point: 209° C.-214° C.; C29H29ClN2O (M=457.01); calc.: molecular ion peak (M+H)+: 457/459 (Cl); found: molecular ion peak (M+H)+: 457/459 (Cl); Rf value: 0.60 (silica gel, dichloromethane/methanol (90:10)).

Workup

  1. additionis added
  2. stirringthe reaction mixture is stirred for 16 hours
  3. customThe reaction mixture is evaporated down
  4. customThe purification

Sources & evidence

ORD record
ord-958388c3521a4fd79646ef6c4f0009f8
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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