Methanol → HCID 59265956, compound

HRID 909372Notes

Reaction equation

HRID 909372 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-8cbb3d73946442c6ae0874e431eddebf
Source dataset
uspto-grants-2011_09
Patent number
US08017788B2

Reaction notes

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