2-Aminothiazole → HCID 21537677, compound

HRID 1076558Notes

Reaction equation

HRID 1076558 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:14][CH3:15])[N:11]=[C:12]([CH3:13])[C:7]2=[N:6][C:5]=1[C:16](Cl)=[O:17])[CH3:2].[NH2:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[N:9]=[C:8]2[N:10]([CH2:14][CH3:15])[N:11]=[C:12]([CH3:13])[C:7]2=[N:6][C:5]=1[C:16]([NH:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1)=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8471TriethylamineHCID 21537685HCID 21537685, compound

Product 1

HCID 21537677HCID 21537677, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

15.75 g. of 6-ethoxy-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]-pyrazine-5-carbonyl chloride (0.058 mol.) are dissolved in 150 ml. of dry toluene. To this well cooled solution (ice/sodium chloride) a solution of 6.4 g. of 2-aminothiazole (0.638 mol.) and 6.5 g. of triethylamine (0.638 mol.) in 260 ml. of dry toluene is added dropwise under stirring. The reaction temperature is kept at -5° to -10°. Then stirring is continued at room temperature for 1 hour and at 50° for 1 hour. The precipitated triethylamine hydrochloride is filtered off and the toluene filtrate is removed in vacuo. Recrystallization of the residual 6-ethoxy-1-ethyl-3-methyl-N-2-thiazolyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxamide gives 15.4 g. of product (78%), m.p. 158°-159°.

Workup

  1. customis kept at -5° to -10°
  2. stirringThen stirring
  3. filtrationThe precipitated triethylamine hydrochloride is filtered off
  4. customthe toluene filtrate is removed in vacuo
  5. customRecrystallization of the residual 6-ethoxy-1-ethyl-3-methyl-N-2-thiazolyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxamide
  6. customgives 15.4 g

Sources & evidence

ORD record
ord-b1e17000cc44430f92b85183929a1e9a
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

Loading…