Triethylamine → HCID 24958733, compound

HRID 244445Notes

Reaction equation

HRID 244445 reaction equation
[C:1]([C:3]1[N:4]([CH2:30][C:31]([OH:33])=O)[CH:5]=[C:6]([C:8]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:18]=[CH:17]3)([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:7]=1)#[N:2].C([N:36](CC)CC)C.[Cl-].[NH4+].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:1]([C:3]1[N:4]([CH2:30][C:31]([NH2:36])=[O:33])[CH:5]=[C:6]([C:8]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[N:19]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:18]=[CH:17]3)([OH:13])[C:9]([F:12])([F:11])[F:10])[CH:7]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724699PyBOPHCID 59437287HCID 59437287, compound

Product 1

HCID 24958733HCID 24958733, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-cyano-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrol-1-yl)acetic acid (95 mg, 0.2 mmol, 1 equiv.) and triethylamine (0.16 mL, 1.2 mmol, 6 equiv.) in 2 mL of DMF was added ammonium chloride (67 mg, 1.2 mmol, 6 equiv.) followed by PyBOP (113 mg, 0.22 mmol, 1.1 equiv.) After stirring overnight, the reaction was then filtered into an HPLC vial and purified by reverse phase HPLC (15-95% CH3CN/water+0.1% TFA). The desired fractions were combined and the CH3CN was removed. The aqueous was basified with saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 50 mg (53%) of the title compound as a yellow foam. MS m/z 458.22 (MH+).

Workup

  1. filtrationthe reaction was then filtered into an HPLC vial
  2. custompurified by reverse phase HPLC (15-95% CH3CN/water+0.1% TFA)
  3. customthe CH3CN was removed
  4. extractionextracted with EtOAc
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83bd1a116a0547b28f3e4b86842a14fe
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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