Guanidine Hydrochloride → HCID 178513068, compound

HRID 1766154Notes

Reaction equation

HRID 1766154 reaction equation
[Na].Cl.[NH2:3][C:4]([NH2:6])=[NH:5].Cl.Cl[C:9]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:12]=1)=[O:10]>CO>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[CH:29][C:20]=1[N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]([NH:5][C:4]([NH2:6])=[NH:3])=[O:10])=[CH:12]1

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 21110072HCID 21110072, compound

Product 1

HCID 178513068HCID 178513068, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.477 g (20.73 mmol) of sodium (washed beforehand in toluene) was gradually added to 40 cm3 of methanol at a temperature in the region of 20° C. under an argon atmosphere. After dissolving with stirring, 2.021 g (20.74 mmol) of guanidine hydrochloride were added and the mixture was stirred at a temperature in the region of 20° C. for 2 h. The reaction mixture was filtered and then concentrated to dryness under reduced pressure (2.7 kPa), and the residue was subsequently taken up in a mixture of 70 cm3 of tetrahydrofuran and 70 cm3 of dichloromethane under an argon atmosphere at a temperature in the region of 20° C. 3.46 mmol of 3-chlorocarbonyl-1-(quinolin-2-yl)-1H-pyrrolo[2,3-b]pyridine hydrochloride were added thereto with stirring. After stirring at a temperature in the region of 20° C. for 15 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa). The solid residue was taken up in 100 cm3 of water and stirred for 2 h and then the insoluble material was filtered off. The solid obtained was dried and then triturated in 20 cm3 of cyclohexane. The solid was filtered off and then dried at a temperature in the region of 20° C. under reduced pressure (2.7 kPa), and 0.921 g of N-[1-(quinolin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine was thus obtained in the form of a light yellow solid melting at 242° C. 1H N.M.R. spectrum (300 MHz, (CD3)2SO, δ in ppm): from 6.20 to 7.30 (very broad unresolved peak, 2H), 7.39 (dd, J=8 and 5 Hz, 1H), 7.63 (broad t, J=7.5 Hz, 1H), 7.84 (broad t, J=7.5 Hz, 1H), 8.03 and 8.07 (2 broad d, J=7.5 Hz, each 1H), 8.48 (dd, J=5 and 1.5 Hz, 1H), 8.64 (d, J=9 Hz, 1H), 8.89 (dd, J=8 and 1.5 Hz, 1H), 9.06 (s, 1H), 9.21 (d, J=9 Hz, 1H).

Workup

  1. dissolutionAfter dissolving
  2. stirringthe mixture was stirred at a temperature in the region of 20° C. for 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. additionthe residue was subsequently taken up in a mixture of 70 cm3 of tetrahydrofuran and 70 cm3 of dichloromethane under an argon atmosphere at a temperature in the region of 20° C
  6. stirringwith stirring
  7. stirringAfter stirring at a temperature in the region of 20° C. for 15 h
  8. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  9. stirringstirred for 2 h
  10. filtrationthe insoluble material was filtered off
  11. customThe solid obtained
  12. customwas dried
  13. customtriturated in 20 cm3 of cyclohexane
  14. filtrationThe solid was filtered off
  15. dry with materialdried at a temperature in the region of 20° C. under reduced pressure (2.7 kPa), and 0.921 g of N-[1-(quinolin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine

Sources & evidence

ORD record
ord-dd8aec47cd9c4cebaae70edaa83324ff
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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