Methanol → HCID 59265956, compound

HRID 1927201Notes

Reaction equation

HRID 1927201 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@@H:9]2[S:13][CH3:14])=[CH:4][N:3]=1.[N:15]#[C:16][NH2:17].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.CO>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[S:13]([CH3:14])=[N:17][C:16]#[N:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 9864CyanamideHCID 12217721Iodo benzene diacetateHCID 87316434HCID 87316434, compound

Product 1

HCID 59265956HCID 59265956, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

cis-2-Chloro-5-(2-methylthiocyclopentyl)pyridine (0.15 g, 0.64 mmol) was dissolved in CH2Cl2 (3 mL) in a 50 mL round bottom flask and treated with cyanamide (0.035 g, 0.83 mmol). The mixture was cooled in an ice bath under nitrogen and treated with iodobenzene diacetate (0.28 g, 0.86 mmol) and allowed to stir for 2 h by which time the reaction was judged complete by TLC (CH2Cl2:MeOH/20:1). The reaction mixture was concentrated to low volume and purified by flash silica gel chromatography (CH2Cl2:MeOH/20:1) to give cis-[2-(6-chloropyridin-3-yl)cyclopentyl](methyl)-λ4-sulfanylidenecyanamide (0.145 g, 85%) as an oily 1:1 mixture of diastereomers: LC/MS (ESI) m/z 267, 1H NMR (300 MHz, CDCl3) δ 8.31 (d, 2H, J=2.7 Hz), 7.70 (dd, 1H, J=8.4, 2.7 Hz), 7.63 (dd, 1H, J=8.4, 2.7 Hz), 7.40 (d, 1H, J=8.4 Hz), 7.32 (d, 1H, J=8.4 Hz), 3.96 (m, 1H), 3.81 (m, 1H), 3.67-3.51 (m, 2H), 2.73 (s, 3H), 2.59 (m, 1H), 2.45 (s, 3H), 2.40-1.95 (m, 9H), 1.85 (m, 2H).

Workup

  1. temperatureThe mixture was cooled in an ice bath under nitrogen
  2. concentrationThe reaction mixture was concentrated to low volume
  3. custompurified by flash silica gel chromatography (CH2Cl2:MeOH/20:1)

Sources & evidence

ORD record
ord-f42fa683fe604f4e8cb99e56d23e15cc
Source dataset
uspto-grants-2012_05
Patent number
US08183268B2

Reaction notes

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