1,2-Dichloroethane → HCID 59525783, compound

HRID 386076Notes

Reaction equation

HRID 386076 reaction equation
[NH2:1][C:2]([C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][C:10]=2[F:19])[S:6][C:5]=1[NH:20][C:21]1[N:26]=[C:25]([CH:27]([OH:37])[C:28]2[N:29]=[N:30][N:31]([CH2:33][C:34]([O-:36])=O)[CH:32]=2)[CH:24]=[CH:23][CH:22]=1)=[O:3].[K+].C1C=CC2N(O)N=[N:45]C=2C=1.C(Cl)CCl.[NH4+].[Cl-].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:45][C:34](=[O:36])[CH2:33][N:31]1[CH:32]=[C:28]([CH:27]([OH:37])[C:25]2[N:26]=[C:21]([NH:20][C:5]3[S:6][C:7]([C:9]4[CH:14]=[CH:13][C:12]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][C:10]=4[F:19])=[CH:8][C:4]=3[C:2]([NH2:1])=[O:3])[CH:22]=[CH:23][CH:24]=2)[N:29]=[N:30]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68671180HCID 68671180, compound

Product 1

HCID 59525783HCID 59525783, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium{4-[[6-({3-(aminocarbonyl)-5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-thienyl}amino)pyridin-2-yl](hydroxy)methyl]-1H-1,2,3-triazol-1-yl}acetate (96 mg, 0.17 mmol), HOBT (52 mg, 0.34 mmol), EDC (65 mg, 0.34 mmol), and NH4Cl (46 mg, 0.85 mmol) were combined in DMF (3.0 mL), and DIEA (89 μL, 0.51 mmol) was added. The reaction was stirred at room temperature overnight. The solvent was evaporated, and the residue was purified by reverse phase HPLC (10-70% MeCN/water w/0.025% TFA). The isolated product was of insufficient purity, so flash chromatography (dry load, 0-10% MeOH/EtOAc) was performed to afford the title compound as a colorless solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by reverse phase HPLC (10-70% MeCN/water w/0.025% TFA)
  3. dry with materialThe isolated product was of insufficient purity, so flash chromatography (dry load, 0-10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-cd9687bf840b478a849f225940dab42f
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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