HCID 58993671, compound → HCID 24785714, compound

HRID 391472Notes

Reaction equation

HRID 391472 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([O:37][CH3:38])=[C:13]([CH:36]=2)[CH2:14][O:15][CH2:16][C:17]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[CH:5][CH:4]=1)#[N:2].FC(F)(F)C(O)=O.CN(C)C>FC(F)(F)C(O)=O>[CH3:38][O:37][C:12]1[CH:11]=[CH:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[N:8][CH:7]=2)=[CH:36][C:13]=1[CH2:14][O:15][CH2:16][C:17]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 58993671HCID 58993671, compoundHCID 86615909HCID 86615909, compound

Product 1

HCID 24785714HCID 24785714, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-((5-(6-cyanopyridin-3-yl)-2-methoxybenzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (46 mg, 0.090 mmol) was dissolved in trifluoroacetic acid (33% in dichloromethane, 4 mL) and stirred for 1 h. The reaction was concentrated and purified by column chromatography (5% methanol/dichloromethane/2% trimethylamine in ethanol→10% methanol/dichloromethane/2% trimethylamine in ethanol) to give 43.6 mg (quant.) as a colorless oil. The product was tainted with trimethylamine 2,2,2-trifluoroacetate. 1H NMR (500 MHz, CDCl3) δ ppm 9.47 (bs, 1H), 9.25 (bs, 1H), 8.79 (m, 1H), 7.84 (m, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.44 (dd, J=8.5, 2.1, 1H), 7.33 (m, 5H), 7.25 (m, 1H), 6.91 (d, J=8.5 Hz, 1H), 4.47 (s, 2H), 3.82 (s, 3H), 3.48 (s, 2H), 3.27 (bd, 2H), 2.90 (m, 2H), 2.44 (m, 2H), 2.26 (m, 2H); 13C NMR (126 MHz, CDCl3) δ ppm 157.8, 149.3, 140.5, 139.5, 134.3, 131.4, 129.1, 128.5, 128.2, 127.9, 127.2, 126.8, 126.6, 117.7, 110.8, 79.9, 67.7, 55.6, 41.1, 40.6, 29.1. Mass spec.: 414.19 (MH)+. Accurate mass spec.: m/z 414.2188 [MH]+, Δ=1.6 ppm.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography (5% methanol/dichloromethane/2% trimethylamine in ethanol→10% methanol/dichloromethane/2% trimethylamine in ethanol)
  3. customto give 43.6 mg (quant.) as a colorless oil

Sources & evidence

ORD record
ord-315237e26b2d40b7a9740810c4726ee1
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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