Ammonium Chloride → HCID 23652793, compound

HRID 1094498Notes

Reaction equation

HRID 1094498 reaction equation
C[Al](C)C.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])[CH2:8][CH2:7]1.C[O:25][C:26]([C:28]1[C:37]2[C:32](=[CH:33][C:34]([CH2:38][C:39]3[CH:44]=[C:43]([NH:45][C:46](=[O:48])[CH3:47])[N:42]=[CH:41][N:40]=3)=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1)=O.[Cl-].[NH4+]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O>[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:26]([C:28]3[C:37]4[C:32](=[CH:33][C:34]([CH2:38][C:39]5[CH:44]=[C:43]([NH:45][C:46](=[O:48])[CH3:47])[N:42]=[CH:41][N:40]=5)=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)=[O:25])=[CH:15][C:14]=2[C:20]([F:23])([F:21])[F:22])[CH2:8][CH2:7]1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 46838908AP-24592HCID 66639920HCID 66639920, compound

Product 1

HCID 23652793HCID 23652793, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 2 ml trimethylaluminium (2 M in toluene, 4 mMol) is added to a stirred solution of 355 mg (1.3 mMol) 4-(4-methyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenylamine in 20 ml toluene at 10° C. under an argon atmosphere. After 1 h at r t, a solution of 436 mg (1.3 mMol) 6-(6-acetylaminopyrimidin-4-ylmethyl)-naphthalene-1-carboxylic acid methyl ester (Step 9.2) in 5 ml THF is added and the reaction mixture is heated at 90° C. for 45 min. After cooling to 5° C., a solution of sat. aqueous ammonium chloride (50 ml) is added dropwise. The mixture is poured into EtOAc and filtered over hyflo. The separated aq. phase is extracted with EtOAc. The combined organic phases are washed with water and brine, dried (Na2SO4) and concentrated. The crude product is purified by chromatography (SiO2, CH2Cl2/EtOH/NH3 90:9:1) and is recrystallised from hot EtOAc and hexane to afford the title compound as a colourless solid: m.p.: 202-204° C.

Workup

  1. temperatureAfter cooling to 5° C.
  2. filtrationfiltered over hyflo
  3. extractionThe separated aq. phase is extracted with EtOAc
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography (SiO2, CH2Cl2/EtOH/NH3 90:9:1)
  8. customis recrystallised from hot EtOAc and hexane

Sources & evidence

ORD record
ord-11d952e7b57b48bf98e69a89996db038
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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