Hydrogen Bromide → HCID 19875918, compound

HRID 1886406Notes

Reaction equation

HRID 1886406 reaction equation
C(O)(=O)/C=C/C(O)=O.[S:9]1[CH:13]=[C:12]([CH2:14][N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]=[C:16]2[NH:24][CH:25]2[CH2:29][CH2:28][N:27](C(OCC)=O)[CH2:26]2)[N:11]=[CH:10]1.[BrH:35]>O>[BrH:35].[BrH:35].[NH:27]1[CH2:28][CH2:29][CH:25]([NH:24][C:16]2[N:15]([CH2:14][C:12]3[N:11]=[CH:10][S:9][CH:13]=3)[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 131716768HCID 131716768, compound

Product 1

HCID 19875918HCID 19875918, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 157.0 parts of ethyl 3-[[3-(4-thiazolylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-pyrrolidinecarboxylate (E)-2-butenedioate(2:3) and 870 parts of a hydrobromic acid solution 48% in water was stirred for 22 hours at 100° C. After cooling, the precipitate was filtered off and washed with water. The filtrate was evaporated. The residue was taken up three times in methylbenzene and the solvent was evaporated each time. The oily residue was stirred in 2-propanone. The precipitate was filtered off and the filtrate was evaporated. The residue was taken up in boiling ethanol. The clear solution was filtered and the filtrate was allowed to crystalline over weekend while stirring. The crystallized product was filtered off, washed with ethanol and dried in vacuo at 50° C., yielding 106.5 parts (79.4%) of N-(3-pyrrolidinyl)-3-(4-thiazolylmethyl)-3H-imidazo[4,5-b]pyridin-2-amine dihydrobromide; mp. 260.5° C. (compound 38).

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customThe filtrate was evaporated
  5. customthe solvent was evaporated each time
  6. stirringThe oily residue was stirred in 2-propanone
  7. filtrationThe precipitate was filtered off
  8. customthe filtrate was evaporated
  9. filtrationThe clear solution was filtered
  10. stirringwhile stirring
  11. filtrationThe crystallized product was filtered off
  12. washwashed with ethanol
  13. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-acd1f0b75b3848fbba7be005aa7f60b4
Source dataset
uspto-grants-1992_09
Patent number
US05151424

Reaction notes

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