Diisopropylethylamine → HCID 178520267, compound

HRID 45815

Reaction equation

HRID 45815 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:3][CH:2]=1.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>ClCCl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:8]([C:12]3[CH:13]=[C:14]([NH:18][C:28](=[O:29])[CH2:27][C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:31])([F:19])[F:32])=[CH:26][CH:25]=4)[CH:15]=[CH:16][CH:17]=3)=[N:9][NH:10][CH:11]=2)=[CH:5][CH:6]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178507541HCID 178507541, compound

Product 1

HCID 178520267HCID 178520267, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenylamine (80 mg, 0.339 mmol) (prepared as described in Example 6) in dichloromethane (8 mL), were added in the following order: (4-trifluoromethyl-phenyl)-acetic acid (138 mg, 0.678 mmol), DIPEA (131 mg, 174 uL, 1.017 mol) and TBTU (326 mg, 1.017 mol). The reaction mixture was stirred at room temperature for 4 hours. Then it was poured into a solution of saturated NaHCO3, the phases separated, and the organic phase was washed twice with saturated NaHCO3, and twice with water. The organic solvent was evaporated, and the residue taken up with methanol (5 mL). TEA (2 mL) was added, and the solution was stirred at room temperature overnight. After evaporation to dryness the compound was purified by flash chromatography, over silica gel, using dichloromethane-methanol (97:3) as the eluant system. N-[3-(4-Pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-2-(4-trifluoromethyl-phenyl)-acetamide was obtained as a colorless solid (125 mg, 87%).

Workup

  1. additionwere added in the following order
  2. customthe phases separated
  3. washthe organic phase was washed twice with saturated NaHCO3
  4. customThe organic solvent was evaporated
  5. additionTEA (2 mL) was added
  6. stirringthe solution was stirred at room temperature overnight
  7. customAfter evaporation to dryness the compound
  8. customwas purified by flash chromatography, over silica gel

Sources & evidence

ORD record
ord-48047db9bb974de3bfc46ebafbf75e99
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Linked notes

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