1-Aminocyclopentanemethanol → HCID 178527184, compound

HRID 2268742Notes

Reaction equation

HRID 2268742 reaction equation
Cl[C:2]1[NH:7][C:6]2[CH:8]=[C:9]([Cl:11])[S:10][C:5]=2[S:4](=[O:13])(=[O:12])[N:3]=1.[NH2:14][C:15]1([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]1>C(O)C>[Cl:11][C:9]1[S:10][C:5]2[S:4](=[O:13])(=[O:12])[N:3]=[C:2]([NH:14][C:15]3([CH2:20][OH:21])[CH2:19][CH2:18][CH2:17][CH2:16]3)[NH:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 663071-AminocyclopentanemethanolHCID 118320583,6-Dichloro-4h-thieno[3,2-e][1,2,4]thiadiazine 1,1-dioxide

Product 1

HCID 178527184HCID 178527184, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,6-dichloro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (0.5 g, 1.95 mmol) and (1-aminocyclopentyl)-methanol (0.45 g, 3.9 mmol) in ethanol (4 ml) was stirred for 21 h at 120° C. in a sealed flask. The cooled solution was concentrated in vacuo and the residue dissolved in 1N sodium hydroxide (40 ml) followed by treatment with decolourising charcoal. After filtration, the clear solution was acidified to pH <2 with 4M hydrochloric acid and the precipitate was filtered off and recrystallised from ethanol and finally purified by chromatography (dichloromethane/methanol (19:1)) to give 70 mg (10%) of the pure title compound; mp 213-214° C.; 1H-NMR (DMSO-d6): δ1.45-2.0 (m, 8H), 3.53 (s, 2H), 5.05 (br s, 1H), 6.82 (br s, 1H) 7.11 (s, 1H), 10.8 (br s, 1H); MS: m/e 335/337 (M+), 317/319 (M—H2O)+.

Workup

  1. concentrationThe cooled solution was concentrated in vacuo
  2. dissolutionthe residue dissolved in 1N sodium hydroxide (40 ml)
  3. filtrationAfter filtration
  4. filtrationthe precipitate was filtered off
  5. customrecrystallised from ethanol
  6. customfinally purified by chromatography (dichloromethane/methanol (19:1))

Sources & evidence

ORD record
ord-adee1fa0742247f1b538f3709602d78b
Source dataset
uspto-grants-2001_12
Patent number
US06329367B1

Reaction notes

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