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(1,3,5-trimethyl-1H-pyrazol-4-yl)methylamine → [4-(2-o-Tolyl-chroman-6-yloxy)-cyclohexyl]-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-amine

HRID 59774
Notes
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Reaction equation

HRID 59774 reaction equation
[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]3[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]3)[CH:13]=2)[O:8]1.[CH3:26][N:27]1[C:31]([CH3:32])=[C:30]([CH2:33][NH2:34])[C:29]([CH3:35])=[N:28]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]1([CH3:25])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][CH:18]3[CH2:23][CH2:22][CH:21]([NH:34][CH2:33][C:30]4[C:29]([CH3:35])=[N:28][N:27]([CH3:26])[C:31]=4[CH3:32])[CH2:20][CH2:19]3)[CH:13]=2)[O:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2776430(1,3,5-trimethyl-1H-pyrazol-4-yl)methylamineHCID 5003444Sodium cyanoborohydrideHCID 90389985HCID 90389985, compound

Product 1

HCID 90390297[4-(2-o-Tolyl-chroman-6-yloxy)-cyclohexyl]-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-amineYield 95.7%

Reagents, catalysts & solvents 2

HCID 176Acetic Acid
Solvent
HCID 887MethanolSolvent

Procedure

To a solution of 100 mg 4-(2-o-tolyl-chroman-6-yloxy)-cyclohexanone (0.30 mmol) in 2 ml of methanol and 0.15 ml of acetic acid at room temperature 124 mg (1,3,5-trimethyl-1H-pyrazol-4-yl-methyl)amine (0.89 mmol) and 56 mg of sodium cyanoborohydride (0.89 mmol) were added in one portion and stirring at room temperature was continued for 2 h. Volatile components were removed under reduced pressure and the resulting residue dissolved in dichloromethane. The organic layer was washed with aqueous 2N sodium hydroxide solution and saturated aqueous sodium chloride solution. The organic layer was dried with sodium sulfate and filtered, and the solvent removed under reduced pressure. The crude product was purified by reversed phase HPLC. 132 mg of the title compound were isolated.

Workup

  1. customVolatile components were removed under reduced pressure
  2. dissolutionthe resulting residue dissolved in dichloromethane
  3. washThe organic layer was washed with aqueous 2N sodium hydroxide solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe crude product was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-bc102e7b04324135b795bff309f724c0
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440941B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes