Hydrochloric Acid → HCID 69885612, compound

HRID 47760Notes

Reaction equation

HRID 47760 reaction equation
[ClH:1].Cl.[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][CH:10]1[CH2:14][S:13][C:12]([NH2:15])=[N:11]1.Cl>C(O)C.C(OCC)C>[ClH:1].[ClH:1].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][C@@H:10]1[CH2:14][S:13][C:12]([NH2:15])=[N:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22747880HCID 22747880, compound

Product 1

HCID 69885612HCID 69885612, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A racemic mixture of 2.9 g of (4RS)-4-(2-pyrazinylmethyl)-4,5-dihydro-2-thiazolyl-amine dihydrochloride is separated on a Chiralcel OD10μ column in a heptane/ethanol/triethylamine mixture (80/20/0.1 by volume). The fractions containing the expected product are concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. The residue obtained is dissolved in 5 cm3 of ethanol, followed by addition of 6 cm3 of hydrochloric acid dissolved in diethyl ether and 15 cm3 of diethyl ether. After filtration, washing with 15 cm3 of diethyl ether and drying, 0.371 g of (+)-(4R)-4-(2-pyrazinyl-methyl)-4,5-dihydro-2-thiazolylamine dihydrochloride is obtained in the form of a beige-colored solid melting at 154° C. [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ in ppm): 3.22 (d, J=6.5 Hz: 2H); 3.45 (dd, J=11.5 and 5.5 Hz: 1H); 3.75 (dd, J=11.5 and 8 Hz: 1H); 4.73 (mt: 1H); 8.60 (broad d, J=2.5 Hz: 1H); 8.63 (dd, J=2.5 and 1.5 Hz: 1H); 8.66 (broad s; 1H); 9.09 (unresolved complex: 1H); 9.58 (unresolved complex: 1H); 9.95 (broad s: 1H); (αD20=+46.3+/−1.1 at a concentration of 0.5% in methanol)].

Workup

  1. customis separated on a Chiralcel OD10μ column in a heptane/ethanol/triethylamine mixture (80/20/0.1 by volume)
  2. additionThe fractions containing the expected product
  3. concentrationare concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C
  4. customThe residue obtained
  5. filtrationAfter filtration
  6. washwashing with 15 cm3 of diethyl ether
  7. customdrying

Sources & evidence

ORD record
ord-7765f8bc628c4e8d895d9663374722c9
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Reaction notes

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