Triethylamine → HCID 178432422, compound

HRID 2268746Notes

Reaction equation

HRID 2268746 reaction equation
[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6](F)[NH:5][C:4]=2[CH:3]=1.Cl.[CH3:15][C:16]1([NH2:21])[CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:21][C:16]3([CH3:15])[CH2:20][CH2:19][CH2:18][CH2:17]3)[NH:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109226916-Chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxideHCID 115064601-methylcyclopentan-1-amine Hydrochloride

Product 1

HCID 178432422HCID 178432422, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 6-chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (0.60 g, 2.5 mmol), 1-methylcyclopentylamine hydrochloride (0.5 g, 3.7 mmol) and triethylamine (1.03 ml, 7.4 mmol) in ethanol (2.5 ml) was stirred for 16 h at 50° C. and then for 24 h at 65° C. in a sealed flask. The cooled mixture was concentrated in vacuo and the residue was triturated with water followed by adjustment to pH <2 with 1M hydrochloric acid. The crude product was isolated by filtration, dried and recrystallised from acetic acid to give 208 mg (26%) of the title compound; mp >300° C. (dec.); 1H-NMR (DMSO-d6): δ1.43 (s, 1H), 1,53-1.72 (m, 6H), 1.92-2.10 (m, 2H), 6.91 (br s, 1H), 7.10 (s, 1H), 10.52 (br s, 1H).

Workup

  1. waitfor 24 h at 65° C. in a sealed flask
  2. concentrationThe cooled mixture was concentrated in vacuo
  3. customthe residue was triturated with water
  4. customThe crude product was isolated by filtration
  5. customdried
  6. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-249d2d0a43c643f1b254ce7e03560857
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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