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2-(Isocyanatomethyl)furan → 1-(5-(5-(6-(benzyloxy)pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3-(furan-2-ylmethyl)urea

HRID 64183
Notes
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Reaction equation

HRID 64183 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]([NH2:36])[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.[CH2:39]([N:45]=[C:46]=[O:47])[C:40]1[O:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[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]([NH:36][C:46]([NH:45][CH2:39][C:40]5[O:44][CH:43]=[CH:42][CH:41]=5)=[O:47])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 42238112-(Isocyanatomethyl)furanHCID 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 1177778291-(5-(5-(6-(benzyloxy)pyridin-3-yl)-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-3-(furan-2-ylmethyl)ureaYield 86%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

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 (75 mg, 0.148 mmol) in DCM was added furfuryl isocyanate (19 mg, 0.163 mmol, 1.1 eq.). The mixture was stirred overnight and quenched and extracted as in Example 2(b). The solvent was distilled off to afford the crude residue which was recrystallized in ether to afford the title compound in 86% yield (80 mg).

Workup

  1. customquenched
  2. extractionextracted as in Example 2(b)
  3. distillationThe solvent was distilled off
  4. customto afford the crude residue which
  5. customwas recrystallized in ether

Sources & evidence

ORD record
ord-eb206135766e4ef4ac3d459e0a1b1803
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes