2-Aminothiazole → HCID 21537687, compound

HRID 1076551Notes

Reaction equation

HRID 1076551 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:15](Cl)=[O:16])[CH3:2].[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:7]2=[N:6][C:5]=1[C:15]([NH:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 21537693HCID 21537693, compound

Product 1

HCID 21537687HCID 21537687, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 15.3 g. of 6-ethoxy-1-ethyl-1H-pyrazolo-[3,4-b]pyrazine-5-carbonyl chloride (0.06 mol.), 6.6 g. of 2-amino-thiazole (0.66 mol.) and 9.1 ml. of triethylamine (0.66 mol.) in 400 ml. of dry benzene are refluxed for 21/2 hours. After cooling the reaction mixture, the precipitated triethylamine hydrochloride is filtered off and the filtrate is evaporated to dryness. The crude 6-ethoxy-1-ethyl -N-2-thiazolyl-1H-pyrazolo-[3,4-b]pyrazine-5-carboxamide is recrystallized from ethyl acetate, m.p. 151°-152°, yield 9.9 g. (52 %).

Workup

  1. additionA mixture of 15.3 g
  2. temperatureAfter cooling the reaction mixture
  3. filtrationthe precipitated triethylamine hydrochloride is filtered off
  4. customthe filtrate is evaporated to dryness
  5. customThe crude 6-ethoxy-1-ethyl -N-2-thiazolyl-1H-pyrazolo-[3,4-b]pyrazine-5-carboxamide is recrystallized from ethyl acetate, m.p. 151°-152°, yield 9.9 g

Sources & evidence

ORD record
ord-ba47830736cb4a2fa5ca644b05f9ce97
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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