Phosgene → Methyl 2-(1-(bis(4-methoxyphenyl)methyl)-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-4-yloxy)-4-fluorobenzoate

HRID 624436Notes

Reaction equation

HRID 624436 reaction equation
[NH2:1][C:2]1[C:19]([NH:20][CH:21]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:18][CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(N(C(C)C)C(C)C)C.[C:47](Cl)(Cl)=[O:48]>ClCCl.C1(C)C=CC=CC=1>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([CH:21]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:3]([O:4][C:5]4[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:6]=4[C:7]([O:9][CH3:10])=[O:8])[C:2]=3[NH:1][C:47]2=[O:48])=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 67145036Methyl 2-(2-amino-3-(bis(4-methoxyphenyl)methylamino)phenoxy)-4-fluorobenzoate

Product 1

HCID 67227808Methyl 2-(1-(bis(4-methoxyphenyl)methyl)-2-oxo-2,3-dihydro-1h-benzo[d]imidazol-4-yloxy)-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of EXAMPLE 368C (0.58 g) and N-ethyl-N-isopropylpropan-2-amine (0.804 ml) in dichloromethane (8 mL) was cooled with an ice bath. Then, a 20 wt % solution of phosgene in toluene (0.850 mil) was added dropwise. The mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with 5% aq. NaHCO3. The material was then absorbed on silica and purified on a silica gel column eluting with 50% ethyl acetate in hexane to provide the title compound.

Workup

  1. washwashed with 5% aq. NaHCO3
  2. customThe material was then absorbed on silica
  3. custompurified on a silica gel column
  4. washeluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-63b373208a8f4801999bd0194eece7d8
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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