Guanidine → HCID 178482792, compound

HRID 1766162Notes

Reaction equation

HRID 1766162 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:11]([C:18]([OH:20])=O)=[CH:10]2)[CH:6]=[CH:7][CH:8]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:44][C:45]([NH2:47])=[NH:46]>O1CCCC1>[CH3:21][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[C:11]([C:18]([NH:46][C:45]([NH2:47])=[NH:44])=[O:20])=[CH:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 3520GuanidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 211100511-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Product 1

HCID 178482792HCID 178482792, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1-(3-(Dimethylamino)phenyl)-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 minutes. 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, resulting in 0.004 g of N-[1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]guanidine in the form of a powder melting at 269–271° C. 1H N.M.R. spectrum (300 MHz, (CD3)2SO with addition of a few drops of CD3COOD, δ in ppm): 3.00 (s, 6H), 6.84 (dd, J=8.5 and 2 Hz, 1H), 7.09 (dd, J=8.5 and 2 Hz, 1H), 7.15 (t, J=2 Hz, 1H), 7.39 (t, J=8.5 Hz, 1H), 7.42 (dd, J=8 and 5 Hz, 1H), 8.46 (dd, J=5 and 2 Hz, 1H), 8.55 (dd, J=8 and 2 Hz, 1H), 8.84 (s, 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 minutes
  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-bea7a31bcae147faa4ed937d9ee0e61c
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

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