Pyridine → HCID 178463227, compound

HRID 2053724Notes

Reaction equation

HRID 2053724 reaction equation
CI.[F:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8]N(C)C(=S)C)=[CH:6][CH:5]=1.[C:16]([O:20][C:21](=[O:33])[NH:22][CH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([NH2:32])[CH:30]=2)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].[N:34]1[CH:39]=CC=[CH:36][CH:35]=1>CCOCC>[C:16]([O:20][C:21](=[O:33])[NH:22][CH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([N:32]=[C:35]([NH:34][CH2:39][CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:15][CH:14]=3)[CH3:36])[CH:30]=2)[CH2:25][CH2:24]1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6328Methyl iodideHCID 21074313HCID 21074313, compoundHCID 69224271(6-Amino-indan-1-yl)-carbamic acid tert-butyl ester

Product 1

HCID 178463227HCID 178463227, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add MeI (0.623 g, 4.4 mmol) to a solution of N-4-fluorobenzyl-N-methylthioacetamide (0.662 g, 3.4 mmol) in 10 mL of ether at rt. Stir the mixture for 3 h and evaporate the ether under vacuum. Add (6-aminoindan-1-yl)carbamic acid tert-butyl ester (0.7 g, 2.28 mmol) followed by 5 mL of pyridine. Stir the resulting mixture for 12 h. Evaporate pyridine and purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2) to give 1.26 g of (6-(1-((4-fluorobenzyl)methylamino)ethylideneamino)indan-1-yl)carbamic acid tert-butyl ester as a light yellow solid; MS 412 (MH+); 1H NMR (CD3OD) d 7.35-7.29 (2H, m), 7.18-7.10 (3H, m), 6.70 (1H, s), 6.65 (1H, d, J=7.6 Hz), 5.06 (1H, t, J=6.8 Hz), 4.69 (2H, s), 3.05 (3H, s), 2.97-2.91 (1H, m), 2.84-2.77 (1H, m), 2.55-2.48 (1H, m), 1.97 (3H, s), 1.52 (9H, s).

Workup

  1. customevaporate the ether under vacuum
  2. stirringStir the resulting mixture for 12 h
  3. customEvaporate pyridine and purify the residue by column chromatography (silica gel, 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-bd0acbc5bf9d4460944e05b9c9a00ac7
Source dataset
uspto-grants-2008_02
Patent number
US07326731B2

Reaction notes

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