1,2-Dichloroethane → HCID 178428506, compound

HRID 505562Notes

Reaction equation

HRID 505562 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:7]([CH2:13]N)=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].[Cl-].[NH4+].[NH:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[C:23]([CH2:30][C:31]([OH:33])=O)=[N:22]1.C1C=[N:38]C2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:5][C:6]1[C:7]([CH2:13][CH:30]([C:23]2[C:24]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[NH:21][N:22]=2)[C:31]([NH2:38])=[O:33])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 684281901-[3-(3-Bromo-5-chlorophenoxy)-4-methylpyridin-2-yl]methanamineHCID 178525256HCID 178525256, compound

Product 1

HCID 178428506HCID 178428506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-yl]methanamine (125 mg, 0.382 mmol), 1H-pyrazolo[3,4-b]pyridin-3-ylacetic acid compound with ammonium chloride (1:1), (102 mg, 0.443 mmol), HOAT (5.2 mg, 0.038 mmol) and TEA (53 μL, 0.382 mmol) in DMF (2 mL) was added EDC (80 mg, 0.42 mmol), and the mixture was stirred for 2.2 hours. The mixture was then filtered and purified using Waters PrepPak column and eluting with a gradient of 5-95% ACN/H2O with 0.1% TFA. The desired fractions were lyophilized to give title compound.

Workup

  1. filtrationThe mixture was then filtered
  2. custompurified
  3. washeluting with a gradient of 5-95% ACN/H2O with 0.1% TFA

Sources & evidence

ORD record
ord-cf992e5e9c854bca913e77e0bd2736c4
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

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