1,2-Dichloroethane → HCID 178480500, compound

HRID 1951456Notes

Reaction equation

HRID 1951456 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([NH2:8])[CH:7]=1.[F:17][C:18]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:19]=1[C:20]([NH:22][C:23]1[C:24]([C:28](O)=[O:29])=[N:25][NH:26][CH:27]=1)=[O:21].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[C:6]([NH:8][C:28]([C:24]2[C:23]([NH:22][C:20](=[O:21])[C:19]3[C:18]([F:17])=[CH:34][CH:33]=[CH:32][C:31]=3[F:35])=[CH:27][NH:26][N:25]=2)=[O:29])[CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 196271685-Fluoro-2-(1-methyl-piperidin-4-yloxy)-phenylamineHCID 178524954HCID 178524954, compound

Product 1

HCID 178480500HCID 178480500, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-fluoro-2-(1-methyl-piperidin-4-yloxy)-phenylamine) (0.049 g, 0.22 mmol) was combined with 4-(2,6-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (0.053 g, 0.20 mmol), EDC (0.048 g, 0.25 mmol), HOBt (0.034 g, 0.25 mmol) and DMF (1 ml) and the resulting reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was reduced in vacuo and purified by preparative LC/MS to give 4-(2,6-Difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid[5-fluoro-2-(1-methyl-piperidin-4-yloxy)-phenyl]amide as a buff solid. (0.010 g, 11%) (LC/MS: Rt 2.19, [M+H]+ 474.27).

Workup

  1. customthe resulting reaction mixture
  2. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-3d415a1a0e414da78e6e983a0f5cbf31
Source dataset
uspto-grants-2013_03
Patent number
US08404718B2

Reaction notes

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