N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine → HCID 44232235, compound

HRID 1044333Notes

Reaction equation

HRID 1044333 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH:11]([F:13])[F:12])=[CH:4][CH:3]=1.O[C:15]1[CH2:19][O:18][C:17](=[S:20])[CH:16]=1>C(O)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:10][CH:11]([F:13])[F:12])[C:15]2[CH2:19][O:18][C:17](=[S:20])[CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 44604123N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamineHCID 1361842464-hydroxyfuran-2(5H)-thione

Product 1

HCID 44232235HCID 44232235, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

105 mg (0.506 mmol) of N-[(6-chloropyridin-3-yl)methyl]-2,2-difluoroethanamine (which can be prepared according to: WO 2007/115644 A1, WO 2008/009360 A2) were added to 20 mg (0.169 mMol) of 4-hydroxyfuran-2(5H)-thione (known from: R. Labruère et al., Synthesis 4163-4166, 2006) in 0.5 ml of acetic acid, and the mixture was stirred at room temperature for 14 days. Concentration under reduced pressure and purification of the residue by preparative HPLC (RP18, CH3CN—H2O) gave 15 mg (yield: 28.8% of theory) of 4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-thione.

Workup

  1. concentrationConcentration
  2. customunder reduced pressure and purification of the residue by preparative HPLC (RP18, CH3CN—H2O)

Sources & evidence

ORD record
ord-41b80943c48249bfbf32e485443092a3
Source dataset
uspto-grants-2013_10
Patent number
US08563584B2

Reaction notes

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