ethyl (2-amino-4-methyl-1,3-thiazol-5-yl)acetate → HCID 53873336, compound

HRID 1902561Notes

Reaction equation

HRID 1902561 reaction equation
[I-].CS[C:4]1[S:5][CH2:6][C@@H:7]2[CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH2:9][N+:8]=12.[NH2:17][C:18]1[S:19][C:20]([CH2:24][C:25]([O:27][CH2:28]C)=[O:26])=[C:21]([CH3:23])[N:22]=1>N1C=CC=CC=1>[CH3:28][O:27][C:25]([CH2:24][C:20]1[S:19][C:18]([N:17]=[C:4]2[N:8]3[CH2:9][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[CH2:16][C@H:7]3[CH2:6][S:5]2)=[N:22][C:21]=1[CH3:23])=[O:26]

Participants

4

Reactant 2

HCID 831434ethyl (2-amino-4-methyl-1,3-thiazol-5-yl)acetateHCID 12874874(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo[3,4-b]isoquinolinium iodide

Product 1

HCID 53873336HCID 53873336, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(S)-3-Methylthio-1,5,10,10a-tetrahydrothiazolo-[3,4-b]isoquinolinium iodide (10 g) is added to a solution of ethyl (2-amino-4-methylthiazol-5-yl)acetate (5.5 g) in pyridine (150 cc). After 48 hours at a temperature of the order of 20° C., the solution is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C. The residue is dissolved in a mixture of methylene chloride (200 cc) and N sodium hydroxide solution (100 cc). The organic phase is washed with water (2×100 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C. The residue is crystallised by dissolving it in boiling ethanol (120 cc) and cooling to 0° C. The resulting crystals are filtered off, washed with ethanol (30 cc) and diethyl ether (20 cc) and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa) to yield (S)-3-[(5-methoxycarbonylmethyl-4-methylthiazol-2-yl)imino]-1,5,10,10a-tetrahydrothiazolo[3,4-b]-isoquinoline (8.1 g), as a white solid, m.p.=66° C.

Workup

  1. concentrationthe solution is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C
  2. dissolutionThe residue is dissolved in a mixture of methylene chloride (200 cc) and N sodium hydroxide solution (100 cc)
  3. washThe organic phase is washed with water (2×100 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 40° C
  7. customThe residue is crystallised
  8. dissolutionby dissolving it
  9. filtrationThe resulting crystals are filtered off
  10. washwashed with ethanol (30 cc) and diethyl ether (20 cc)
  11. customdried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-fba1fe0084e7419baab52a01e6cbfcee
Source dataset
uspto-grants-1982_12
Patent number
US04363909

Reaction notes

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