1,2-Dichloroethane → HCID 178428596, compound

HRID 505568Notes

Reaction equation

HRID 505568 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:12][C:13]1[C:14]([NH:20][NH2:21])=[N:15][CH:16]=[CH:17][C:18]=1[CH3:19].[Cl-].[NH4+].[NH:28]1[C:32]2=[N:33][CH:34]=[CH:35][CH:36]=[C:31]2[C:30]([CH2:37][C:38](O)=[O:39])=[N:29]1.C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[O:12][C:13]1[C:14]([NH:20][NH:21][C:38](=[O:39])[CH2:37][C:30]2[C:31]3[C:32](=[N:33][CH:34]=[CH:35][CH:36]=3)[NH:28][N:29]=2)=[N:15][CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 684264713-(3-Bromo-5-chlorophenoxy)-2-hydrazino-4-methylpyridine trifluoroacetateHCID 178525256HCID 178525256, compound

Product 1

HCID 178428596HCID 178428596, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-bromo-5-chlorophenoxy)-2-hydrazino-4-methylpyridine trifluoroacetate (112 mg, 0.253 mmol), 1H-pyrazolo[3,4-b]pyridin-3-ylacetic acid compound with ammonium chloride (1:1), (67.6 mg, 0.253 mmol), HOAT (6.89 mg, 0.051 mmol) and TEA (106 μL, 0.759 mmol) in DMF (1 mL) was added EDC (58.2 mg, 0.304 mmol) and the resulting mixture was stirred for 2 hours. The mixture was then filtered and purified on a Luna column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA) to give the title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. custompurified on a Luna column (10μ, C18, 250×21.2 cm)
  3. washeluting with 5-95% ACN/water with 0.1% TFA)

Sources & evidence

ORD record
ord-b4d3c2e2e7f14512861a1b716a5e0dd1
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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