Trityl chloride → HCID 178492069, compound

HRID 2422980Notes

Reaction equation

HRID 2422980 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:31])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]5=[O:30])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:32]#[N:33])=[N:10]2)=[CH:5][CH:4]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[NH4+].[Cl-].C(Cl)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:31])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH:29]=[CH:28][CH:27]=[CH:26][C:25]5=[O:30])=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:32]3[NH:36][N:35]=[N:34][N:33]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 6456Trityl chlorideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 10203446HCID 10203446, compound

Product 1

HCID 178492069HCID 178492069, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1(2H)-pyridinyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carbonitrile (0.1 g, 0.23 mmol) in DMF (2 mL) was added NaN3 (19 mg, 0.29 mmol) and NH4Cl (21 mg, 0.38 mmol) and the reaction was heated to 105° C. for 24 h. The reaction was cooled, water (1 mL) was added, and the resulting solid filtered off and dried. The solid was placed in DMF (1 mL) and trityl chloride (60 mg, 0.2 mmol) and pyridine (0.2 mL) were added and stirred for 24 h. The reaction was quenched with water, extracted with EtOAc, and dried (Na2SO4). Purification on silica gel was not successful. The trityl group was removed with TFA (0.5 mL) in CH2Cl2 for 2 h. The solvents were removed and the compound was purified by HPLC and freeze-dried to afford 10 mg (9%) of a white solid; High Resolution Mass Spec (M+H)+ for C25H21N8O3 481.1749.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe resulting solid filtered off
  3. customdried
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialdried (Na2SO4)
  7. customPurification on silica gel
  8. customThe trityl group was removed with TFA (0.5 mL) in CH2Cl2 for 2 h
  9. customThe solvents were removed
  10. customthe compound was purified by HPLC
  11. customfreeze-dried

Sources & evidence

ORD record
ord-76252d04f5c54f08a777b8e5233d92a1
Source dataset
uspto-grants-2011_06
Patent number
US07960411B2

Reaction notes

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