Phenethylamine → HCID 71117993, compound

HRID 2368533Notes

Reaction equation

HRID 2368533 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[CH2:4][S:5][C:6]1[N:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:8]([C:11](O)=[O:12])=[CH:9][N:10]=1.[CH2:26](CN)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH2:35]([N:37](CC)CC)C.CCCP(=O)=O>ClCCl>[CH2:26]([N:37]([CH3:35])[C:11]([C:8]1[N:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6]([S:5][CH2:4][C:3]2[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:2]=2[Cl:1])=[N:10][CH:9]=1)=[O:12])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 16167369Propylphosphoric anhydrideHCID 45287358HCID 45287358, compound

Product 1

HCID 71117993HCID 71117993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-((2-chloro-6-fluorobenzyl)thio)-1-(4-fluorophenyl)-1H-imidazole-5-carboxylic acid (88) (50 mg, 0.13 mmol), N-benzylmethylamine (16 mg, 0.13 mmol), triethylamine (0.12 mL, 0.79 mmol) and propylphosphonic anhydride (T-3-P)(50% in ethyl acetate, 0.12 mL, 0.20 mmol) in dichloromethane (1.5 mL) was stirred overnight at room temperature. The reaction was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (50%-100% EtOAc in hexanes) to give N-benzyl-2-((2-chloro-6-fluorobenzyl)thio)-1-(4-fluorophenyl)-N-methyl-1H-imidazole-5-carboxamide (500). 1H NMR (400 MHz, CDCl3) δ: 7.37-7.25 (m, 4H), 7.20-6.99 (m, 8H), 6.93-6.90 (m, 1H), 4.64 (s, 2H), 4.45 (s, 2H), 2.96 (s, 3H). LC-MS ESI m/z; found 484.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (50%-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-027e5616f92246e6948debd971e7478f
Source dataset
uspto-grants-2014_04
Patent number
US08703776B2

Reaction notes

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