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N-cyclopropyl-2-oxooxazolidine-3-sulfonamide → 1-(5-(5-(6-(benzyloxy)pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3-cyclopropyl sulfuric diamide

HRID 64189
Notes
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Reaction equation

HRID 64189 reaction equation
[CH2:1]([O:8][CH:9]1[NH:14][CH:13]=[C:12]([C:15]2[CH:38]=[CH:37][C:18]3[N:19]([C:22]4[CH:23]=[C:24](N)[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=5[F:35])[CH:27]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:39]1([NH:42][S:43]([N:46]2CCOC2=O)(=[O:45])=[O:44])[CH2:41][CH2:40]1>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:38]=[CH:37][C:18]3[N:19]([C:22]4[CH:23]=[C:24]([CH:40]5[CH:39]([NH:42][S:43](=[O:44])(=[O:45])[NH2:46])[CH2:41]5)[CH:25]=[C:26]([C:28]5[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=5[F:35])[CH:27]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 89500324N-cyclopropyl-2-oxooxazolidine-3-sulfonamideHCID 895018005-(5-(6-(benzyloxy)-1,6-dihydropyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-amine

Product 1

HCID 1177778331-(5-(5-(6-(benzyloxy)pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3-cyclopropyl sulfuric diamideYield 10%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(5-(6-(benzyloxy)-1,6-dihydropyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-amine (120 mg, 0.2380 mmol) in pyridine was added N-cyclopropyl-2-oxooxazolidine-3-sulfonamide (78 mg, 0.380 mmol, 1.6 eq.). The mixture was stirred at 50° C. for 16 h, quenched with water and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with 1 N HCl and 1N NaOH, water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to give the product in 10% yield (15 mg).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layer was washed with 1 N HCl and 1N NaOH, water, brine
  4. dry with materialdried over sodium sulphate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-13fa002567264d1c8b38b9f18243ef3b
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447091B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes