Triethylamine → HCID 46186796, compound

HRID 881649Notes

Reaction equation

HRID 881649 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:7]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.[CH2:35]([S:37](Cl)(=[O:39])=[O:38])[CH3:36]>C1COCC1.C(OCC)(=O)C>[CH2:35]([S:37]([NH:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[O:5][C:6]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([I:23])=[CH:19][C:18]=2[F:24])[C:7]=1[C:8]([NH2:10])=[O:9])(=[O:39])=[O:38])[CH3:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 57624911HCID 57624911, compound2×

Product 1

HCID 46186796HCID 46186796, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In analogy to GP 6a, 240 mg of 2-(3-amino-phenoxy)-4-fluoro-6-(2-fluoro-4-iodo-phenylamino)-benzamide (Intermediate 1.4; 0.5 mmol, 1 eq.) were dissolved in 8 mL THF and treated with 0.1 mL triethylamine (0.75 mmol, 1.5 eq.) and 71 μL ethylsulfonyl chloride (0.75 mmol, 1.5 eq.). The reaction mixture was stirred at rt overnight, diluted with ethyl acetate, washed with saturated NaHCO3 solution, dried and concentrated in vacuo. HPLC purification of the residue provided 123 mg (0.22 mmol, 48% yield) of the desired compound.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customHPLC purification of the residue

Sources & evidence

ORD record
ord-c0ead368fd8449d8b4e459cda9bb26ce
Source dataset
uspto-grants-2015_03
Patent number
US08993630B2

Reaction notes

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