4-Aminopyridine → HCID 86732462, compound

HRID 1776435Notes

Reaction equation

HRID 1776435 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[N:11]=2)[N:3]=1.[N:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([C:4]2[N:3]=[C:2]([NH:33][C:30]3[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=3)[C:7]([C:8]#[N:9])=[CH:6][N:5]=2)=[N:11]1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 81531DiisopropylethylamineHCID 86732430HCID 86732430, compound

Product 1

HCID 86732462HCID 86732462, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

73 mg of 4-chloro-2-[1-(2-fluorobenzyl)-1H-indazol-3-yl]pyrimidine-5-carbonitrile (1-14-1, 0.201 mmol, 1. eq.), 22.66 mg of pyridin-4-amine (0.241 mmol, 1.2 eq.), 42 μl of N-ethyl-N-(propan-2-yl)propan-2-amine (0.241 mmol, 1.2 eq.) and 1 ml of N,N-dimethylformamide were stirred at room temperature for 24 hours. The reaction mixture was partitioned between half-saturated aqueous sodium hydrogen carbonate solution and dichloromethane/isopropanol 4:1. The aqueous layer was extracted twice with dichloromethane/isopropanol 4:1. The combined organic layers were washed with brine, dried over a silicon filter and concentrated in vacuo. The residue was purified by flash chromatography and preparative HPLC to yield 24.4 mg (0.06 mmol, 28.9%) of the analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between half-saturated aqueous sodium hydrogen carbonate solution and dichloromethane/isopropanol 4:1
  2. extractionThe aqueous layer was extracted twice with dichloromethane/isopropanol 4:1
  3. washThe combined organic layers were washed with brine
  4. customdried over a silicon
  5. filtrationfilter
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography and preparative HPLC
  8. customto yield 24.4 mg (0.06 mmol, 28.9%) of the analytically pure target compound

Sources & evidence

ORD record
ord-e8bd8c03c25d46fd8a32cacf6be45607
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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