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Ethanesulfonyl chloride → HCID 46195696, compound

HRID 881652
Notes
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Reaction equation

HRID 881652 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][O:6][C:7]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])[C:8]=1[C:9]([NH2:11])=[O:10].[CH2:29]([S:31](Cl)(=[O:33])=[O:32])[CH3:30]>N1C=CC=CC=1.C(OCC)(=O)C>[CH2:29]([S:31]([NH:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[CH2:5][O:6][C:7]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[F:25])[C:8]=1[C:9]([NH2:11])=[O:10])(=[O:33])=[O:32])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 67304831HCID 67304831, compound2×

Product 1

HCID 46195696HCID 46195696, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In analogy to GP 6b, 89 mg of 2-(3-Amino-benzyloxy)-4-fluoro-6-(2-fluoro-4-iodo-phenylamino)-benzamide (Intermediate 3.2; 0.18 mmol, 1 eq.) were dissolved in 0.75 mL pyridine, treated with 34 μL ethylsulfonyl chloride (0.36 mmol, 2 eq.). and stirred at rt for two days. the resulting mixture diluted with ethyl acetate, washed with water and the organic layers dried. Concentration in vacuo was followed by trituration to provide 84 mg of the desired compound (80% yield) with a melting point of 170° C.

Workup

  1. washwashed with water
  2. customthe organic layers dried
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-df4243446bdc4679b84f2721236c09f1
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993630B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes