Dimethylformamide → HCID 22031645, compound

HRID 1792523Notes

Reaction equation

HRID 1792523 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:48]=[CH:47][C:43](C(O)=O)=[CH:42][CH:41]=4)=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1.C1(P([N:63]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:41]=[CH:42][C:43]([NH2:63])=[CH:47][CH:48]=4)=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 22031009HCID 22031009, compound

Product 1

HCID 22031645HCID 22031645, compoundYield 31.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 100 mg 4-{4-[3-(2-pyridyl)imidazo[1,2-a]pyridin-6-yl]-1-trityl-1H-3-pyrazolyl}benzoic acid obtained in Example 48, 44 mg diphenyl phosphoryl azide, 23 mg potassium carbonate, and 4 mL N,N-dimethylformamide was stirred at 80° C. for 6 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated, washed twice with water and then with brine, and dried over anhydrous sodium sulfate. The drying agent was filtered off, the filtrate was evaporated, and the residue was purified by NH silica gel column chromatography (ethyl acetate/methanol), to give 30 mg of the title compound as a pale yellow amorphous.

Workup

  1. customthe organic layer was separated
  2. washwashed twice with water
  3. dry with materialwith brine, and dried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe filtrate was evaporated
  6. customthe residue was purified by NH silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-5856381ae3f04a8089fe7703c3c8e459
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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