Dicyclohexylcarbodiimide → HCID 59108869, compound

HRID 478598Notes

Reaction equation

HRID 478598 reaction equation
[NH2:1][C:2]1[C:3]2[C:4](=[N:12][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[CH:14]=2)[N:5]=[C:6]([Cl:11])[C:7]=1[C:8]([OH:10])=[O:9].[F:24][C:25]1[C:30](O)=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:26]=1[F:35].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CCOC(C)=O>[F:24][C:25]1[C:30]([O:9][C:8]([C:7]2[C:6]([Cl:11])=[N:5][C:4]3=[N:12][N:13]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH:14]=[C:3]3[C:2]=2[NH2:1])=[O:10])=[C:29]([F:32])[C:28]([F:33])=[C:27]([F:34])[C:26]=1[F:35]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 180024944-Amino-6-chloro-2-(4-methoxyphenyl)methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic Acid

Product 1

HCID 59108869HCID 59108869, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) solution of 4-amino-6-chloro-2-(4-methoxyphenyl)methyl-2H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (952 mg, 2.86 mmol) and pentafluorophenol (830 mg) in DMF was added a solution of DCC (620 mg, 3 mmol) in EtOAc (9 mL). After work up the crude product was purified by flash column (silica gel, EtOAc/hexane, 1:1) to give the desired product (1.27 g) as a white solid. LC: 4.64 (Gradient 1), MH+: 499.

Workup

  1. customAfter work up the crude product was purified by flash column (silica gel, EtOAc/hexane, 1:1)

Sources & evidence

ORD record
ord-7c26248fa0ae464faa98d0fc86b31bdf
Source dataset
uspto-grants-2003_11
Patent number
US06642244B2

Reaction notes

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