Trifluoroacetic acid → 2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide

HRID 78830Notes

Reaction equation

HRID 78830 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][C@H:10]1[CH2:14]OC(C)(C)[O:11]1)=[O:6].FC(F)(F)[C:31](O)=[O:32].CCOC(C)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:17]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=2[F:28])=[CH:18][N:19]=1)[C:5]([NH:7][O:8][CH2:9][CH:10]([OH:11])[CH2:14][CH2:31][OH:32])=[O:6]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 866291922-bromo-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-[(2-fluoro-4-iodophenyl)-amino]isonicotinamide

Product 1

HCID 866291932-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo -phenylamino)-isonicotinamide was synthesized as described in General method 3: To a solution of 2-bromo-N-{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy}-5-[(2-fluoro-4-iodophenyl)amino]-isonicotinamide (100.0 mg, 0.18 mmol) in dichloromethane (1 ml) was added trifluoroacetic acid (1 ml) at RT. The reaction mixture was stirred at RT for 30 min, and monitored by TLC (Hex:EtOAc=1:1 and contain TEA). Upon completion, the volatiles were evaporated, and the residue was dissolved in dichloromethane, washed with 5% aq. NaHCO3 to get a precipitate. The residue was filtered, washed with water, and dried to get 53 mg (56%) of 2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo-phenylamino)-isonicotinamide. LC/MS: [8.76 min, 541 (M+1)]

Workup

  1. custom2-Bromo-N-(2,4-dihydroxy-butoxy)-5-(2-fluoro-4-iodo -phenylamino)-isonicotinamide was synthesized
  2. customUpon completion, the volatiles were evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washwashed with 5% aq. NaHCO3
  5. customto get a precipitate
  6. filtrationThe residue was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5659275b7f5747f684f32d3dd6cd5270
Source dataset
uspto-grants-2014_09
Patent number
US08841459B2

Reaction notes

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