Hydrochloric Acid → HCID 178487390, compound

HRID 2410014Notes

Reaction equation

HRID 2410014 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]#[N:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:13]=[N:14][CH:15]=[N:16][CH:17]=3)[NH:9]2)=[CH:5][CH:4]=1.[N-:27]=[N+:28]=[N-:29].[Na+].C(O)(C)C.Cl>[Br-].[Zn+2].[Br-].ClCCl.O>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([C:25]4[NH:29][N:28]=[N:27][N:26]=4)[N:24]=3)=[C:8]([C:12]3[CH:17]=[N:16][CH:15]=[N:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 33557Sodium AzideHCID 86703325HCID 86703325, compound

Product 1

HCID 178487390HCID 178487390, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(6-methoxy-2-pyrimidin-5-yl-1H-indol-3-ylmethyl)pyridine-2-carbonitrile (100 mg), sodium azide (95.2 mg), zinc bromide (82.5 mg), isopropyl alcohol (1.76 mL) and water (1.17 mL) was heated under reflux for 21 hours while stirring. The reaction mixture was left to be cooled. To the reaction mixture were added 1 mol/L hydrochloric acid and dichloromethane. The insoluble material was collected by filtration, washed with 1 mol/L hydrochloric acid and water successively, and then dried under reduced pressure at 50° C. to obtain the title compound (104 mg). 1H-NMR (DMSO-d6) δ ppm: 3.79 (3H, s), 4.48 (2H, s), 6.69 (1H, dd, J=2.1, 8.7 Hz), 6.91 (1H, d, J=2.1 Hz), 7.25-7.35 (1H, m), 7.43 (1H, d, J=8.7 Hz), 7.90 (1H, t, J=7.8 Hz), 7.98-8.05 (1H, m), 9.00-9.20 (3H, m), 11.49 (1H, s). ESI-MS (m/z): 385 (M+H)+

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 hours
  3. waitThe reaction mixture was left
  4. temperatureto be cooled
  5. filtrationThe insoluble material was collected by filtration
  6. washwashed with 1 mol/L hydrochloric acid and water successively
  7. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-1d75c21e646a4d2da971b0274692c30b
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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