Triethylamine → HCID 17973765, compound

HRID 747393Notes

Reaction equation

HRID 747393 reaction equation
Cl.[F:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.Br[CH2:14][C:15]1[C:19]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[NH:18][S:17](=[O:25])(=[O:24])[C:16]=1[C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1>CO>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:16]2[S:17](=[O:25])(=[O:24])[NH:18][C:19]3([CH2:23][CH2:22][CH2:21][CH2:20]3)[C:15]=2[CH2:14][NH:5][CH2:4][CH2:3][F:2])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 17973764HCID 17973764, compound

Product 1

HCID 17973765HCID 17973765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-fluoroethylamine hydrochloride (1.08 g, 10.9 mmol; prepared as described in J. Med. Chem. 9 (1966), 892-911) in 30 mL of absolute MeOH was treated with triethylamine (2.50 mL, 1.76 g, 17.4 mmol) at 0° C. Solid 4-bromomethyl-3-(4-chlorophenyl)-2,2-dioxo-2-thia-1-aza-spiro[4.4]non-3-ene (1.64 g, 4.35 mmol; described during the preparation of Intermediate 6) was added. The resulting mixture was stirred for 16 h at ambient temperature and concentrated to dryness under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane/methanol as eluent to yield the title intermediate. Yield: 1.00 g (64%); MS (IS): 359.1 [M+H]+.

Workup

  1. additionwas added
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-10b479b70c7e49499a473f347276165d
Source dataset
uspto-grants-2008_07
Patent number
US07396846B2

Reaction notes

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