N,N'-Dimethylethylenediamine → HCID 178513490, compound

HRID 64327Notes

Reaction equation

HRID 64327 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2Br)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[C:3]=1[C:27]([NH2:29])=[O:28].CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[O:20]([C:17]1[CH:18]=[CH:19][C:14]([C:4]2[C:3]([C:27]([NH2:29])=[O:28])=[C:2]3[NH:1][C:8]4[CH:9]=[N:10][CH:11]=[CH:12][C:7]=4[N:6]3[N:5]=2)=[CH:15][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 117668112HCID 117668112, compound

Product 1

HCID 178513490HCID 178513490, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-amino-1-(3-bromopyridin-4-yl)-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (3.96 g, 8.8 mmol), CuI (836 mg, 4.4 mmol), N1,N2-dimethylethane-1,2-diamine (77 mg, 0.88 mmol), K3PO4 (5.59 g, 26.4 mmol) in 100 mL of DMF was stirred at 100° C. under N2 for 2 hr, until TLC showed that most of starting material was consumed. After cooling down to RT, the mixture was filtered and concentrated. The residue was chromatographed on 30 g of silica gel using DCM/MeOH (20/1 to 10/1) as eluant to afford 3.2 g (99%) of 2-(4-Phenoxyphenyl)-4H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]pyridine-3-carboxamide as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 12.63 (br s, 1H), 8.85 (s, 1H), 8.46 (s, 1H), 7.96 (d, J=4.6 Hz, 1H), 7.81 (d, J=8.6 Hz, 2H), 7.45 (d, J=7.6 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.20 (t, J=7.6 Hz, 1H), 7.14-7.09 (m, 4H). MS (ESI) m/e [M+1]+ 369.9.

Workup

  1. customwas consumed
  2. temperatureAfter cooling down to RT
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. customThe residue was chromatographed on 30 g of silica gel

Sources & evidence

ORD record
ord-c971a518b1bf46569731ef7b5c2ad5e5
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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