Phenethylamine → n-[4-(3h-Imidazo[4,5-c]pyridin-2-yl)-9h-fluoren-9(r,s)-yl]-phenethyl-amine

HRID 2243309Notes

Reaction equation

[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)C.[N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:20][C:19]=1[C:27]1[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32](=O)[C:31]=2[CH:30]=[CH:29][CH:28]=1.[Na].P([O-])(O)(O)=O.[K+]>C(O)C>[N:18]1[C:26]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[NH:20][C:19]=1[C:27]1[C:39]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]([NH:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 130 °C

Procedure

In a microwave reactor, add 81 μL of 2-phenyl-ethylamine, 18 μL of diethylisopropylamine and 182 μL of titanium tetra-isopropylate to a solution of 84 mg of 4-(3H-imidazo[4,5-c]pyridin-2-yl)-fluoren-9-one, obtained in Example 1, in 0.5 ml of ethanol. Then heat successively at 60° C. for 5 minutes, at 70° C. for 20 minutes, at 100° C. for 15 minutes and finally at 130° C. for 30 minutes. After cooling to room temperature, add 25 mg of sodium cyanohydroborate and stir for 16 hours at room temperature. Pour the reaction mixture into 5 ml of a saturated aqueous solution of potassium dihydrogen phosphate, then extract 3 times with 10 ml of dichloromethane. After purification on silica gel, eluting with mixtures of dichloromethane and methanol (98-2, then 96-4 by volume), we obtain 4.8 mg of N-[4-(3H-imidazo[4,5-c]pyridin-2-yl)-9H-fluoren-9(R,S)-yl]-phenethyl-amine, in the form of a white solid with the following characteristics:

Workup

temperatureAfter cooling to room temperature
extractionextract 3 times with 10 ml of dichloromethane
customAfter purification on silica gel
washeluting with mixtures of dichloromethane and methanol (98-2

Sources & evidence

ORD record: ord-f15116f640884f61adccf009269357ee
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674795B2

Reaction notes

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