Hydrochloric Acid → HCID 21913161, compound

HRID 1008103Notes

Reaction equation

HRID 1008103 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]3N=N[N:17]=[C:9]3[C:8]=2[N:18]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[OH-].[K+]>ClCCl.C(OCC)C>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:19][CH2:20][O:21][CH2:22][C:23]#[C:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 21913055HCID 21913055, compound

Product 1

HCID 21913161HCID 21913161, compoundYield 13.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

The general method described in Part D of Example 109 was followed using 8-ethoxymethyl-5,6-dimethyl-7-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-7H-imidazo[4,5-c]tetrazolo[1,5-a]pyridine (6.47 g, 16.0 mmol) as the starting material. The reaction with triphenyl phosphine (4.61 g, 17.6 mmol) required 41 hours, and the hydrolysis of the intermediate required 18 hours. The crude product (11.6 g) was dissolved in dichloromethane and treated with a 1 M solution of hydrochloric acid in diethyl ether (80 mL). The volatiles were removed under reduced pressure, and the resulting solid was recrystallized from acetonitrile. The crystals were dissolved in water (20 mL), and the solution was adjusted to pH 14 with the addition of 50% aqueous sodium hydroxide to provide a solid that was isolated by filtration. The solid was stirred with 1 M aqueous potassium hydroxide for one hour, isolated by filtration, dried for three days under reduced pressure at 70° C. to provide 0.828 g of 2-ethoxymethyl-6,7-dimethyl-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]pyridin-4-amine as a white powder, mp 129-130° C.

Workup

  1. customthe hydrolysis of the intermediate required 18 hours
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting solid was recrystallized from acetonitrile
  4. dissolutionThe crystals were dissolved in water (20 mL)
  5. additionthe solution was adjusted to pH 14 with the addition of 50% aqueous sodium hydroxide
  6. customto provide a solid
  7. customthat was isolated by filtration
  8. customisolated by filtration
  9. customdried for three days under reduced pressure at 70° C.

Sources & evidence

ORD record
ord-ce313997100c43d4b04d487991e295a3
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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