Diisopropylethylamine → N-Ethyl-2,6-dimethyl-N-[3,3,3-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-hydroxypropyl]benzamide

HRID 551481Notes

Reaction equation

HRID 551481 reaction equation
[CH2:1]([NH:3][CH2:4][C:5]([CH2:11][NH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[N:16][N:17]2[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)([OH:10])[C:6]([F:9])([F:8])[F:7])[CH3:2].C(N(CC)C(C)C)(C)C.[CH3:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([CH3:48])[C:40]=1[C:41](Cl)=[O:42]>ClCCl>[CH2:1]([N:3]([CH2:4][C:5]([CH2:11][NH:12][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[N:16][N:17]2[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)([OH:10])[C:6]([F:8])([F:9])[F:7])[C:41](=[O:42])[C:40]1[C:44]([CH3:48])=[CH:45][CH:46]=[CH:47][C:39]=1[CH3:38])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 890962,6-Dimethylbenzoyl chlorideHCID 593241253-(Ethylamino)-1,1,1-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-propanol

Product 1

HCID 45271025N-Ethyl-2,6-dimethyl-N-[3,3,3-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-hydroxypropyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

3-(Ethylamino)-1,1,1-trifluoro-2-({[1-(4-fluorophenyl)-1H-indazol-4-yl]amino}methyl)-2-propanol (25 mg, 0.063 mmol) was dissolved in anhydrous dichloromethane (0.15 ml). N,N-diisopropylethylamine (0.011 ml, 0.13 mmol) was then added followed by 2,6-dimethylbenzoyl chloride in DCM (10.6 mg, 0.065 mmol as a 100 μl aliquot of 80.8 mg in 0.76 ml DCM) and the mixture stirred at room temperature overnight. The mixture was diluted with dichloromethane, washed successively with aqueous sodium bicarbonate and water and then dried through a hydrophobic frit and evaporated and the crude product purified by mass directed autopreparation (System B). Product containing fractions were partitioned between dichloromethane and aqueous sodium bicarbonate. The aqueous layer was re-extracted with dichloromethane and the combined organic extracts were washed successively water and brine, dried through a hydrophobic frit and evaporated in vacuo to give the title compound (13.1 mg).

Workup

  1. washwashed successively with aqueous sodium bicarbonate and water
  2. customdried through a hydrophobic frit
  3. customevaporated
  4. customthe crude product purified by mass
  5. additionProduct containing fractions
  6. customwere partitioned between dichloromethane and aqueous sodium bicarbonate
  7. extractionThe aqueous layer was re-extracted with dichloromethane
  8. washthe combined organic extracts were washed successively water and brine
  9. customdried through a hydrophobic frit
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-90fb427545dd42a9b6ccaa8c0fec8a7b
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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