Guanidine → HCID 178479500, compound

HRID 1766157Notes

Reaction equation

HRID 1766157 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([OH:18])=O)=[CH:8]1.[ClH:19].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:41][C:42]([NH2:44])=[NH:43]>O1CCCC1>[ClH:19].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([C:16]([NH:43][C:42]([NH2:44])=[NH:41])=[O:18])=[CH:8]1

Participants

6

Reactant 4

HCID 3520GuanidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211100571-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 178479500HCID 178479500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1-(Pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, 0.46 g (2.4 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.027 g (0,2 mmol) of 1-hydroxybenzotriazole were added to 0.59 g (10 mmol) of guanidine in 15 cm3 of tetrahydrofuran under an argon atmosphere. After stirring at a temperature in the region of 20° C. for 16 days, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was triturated in 20 cm3 of methanol and then filtered. The filtrate was concentrated to dryness under reduced pressure (2.7 kPa) and the residue was purified by flash chromatography on silica gel, elution being carried out with a 100% of dichloromethane to dichloromethane/methanol/triethylamine (50/48/2 by volume) gradient over 90 min. After concentrating the fractions comprising the expected product to dryness under reduced pressure (2.7 kPa), the solid obtained was triturated in 20 cm3 of ethanol and filtered off, affording 0.028 g of N-[1-(pyridin-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine hydrochloride in the form of a beige powder melting at 205–207° C. 1H N.M.R. spectrum (300 MHz, (CD3)2SO, 8 in ppm): from 7.30 to 7.45 (m, 2H), 8.08 (ddd, J=9, 8 and 2 Hz, 1H), 8.43 (dd, J=5 and 2 Hz, 1H), 8.59 (dd, J=5 and 2 Hz, 1H), 8.84 (dd, J=8 and 2 Hz, 1H), 8.89 (s, 1H), 8.95 (d, J=9 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  2. customthe residue was triturated in 20 cm3 of methanol
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure (2.7 kPa)
  5. customthe residue was purified by flash chromatography on silica gel, elution
  6. waitbeing carried out with a 100% of dichloromethane to dichloromethane/methanol/triethylamine (50/48/2 by volume) gradient over 90 min
  7. concentrationAfter concentrating the fractions
  8. customthe solid obtained
  9. customwas triturated in 20 cm3 of ethanol
  10. filtrationfiltered off

Sources & evidence

ORD record
ord-b1669b99477c4603bf30e2d1143a872c
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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