1,2-Dichloroethane → [1-(3-Bromo-benzyl)-3-[3-(3-methanesulfonylaminocarbonyl-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester

HRID 410375Notes

Reaction equation

HRID 410375 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].C(Cl)CCl.[Br:10][C:11]1[CH:12]=[C:13]([CH:45]=[CH:46][CH:47]=1)[CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=2)[C:31](O)=[O:32])[C:16]1=[N:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>C(O)(C)(C)C.ClCCl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:41]([O:40][C:38](=[O:39])[N:37]=[C:16]1[N:15]([CH2:14][C:13]2[CH:45]=[CH:46][CH:47]=[C:11]([Br:10])[CH:12]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]1[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:30]([C:31]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:32])[CH:29]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

8

Reactant 3

HCID 111,2-DichloroethaneHCID 72879MethanesulfonamideHCID 674283863-(3-{3-(3-Bromo-benzyl)-2-[tert-butoxycarbonylimino]-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid

Product 1

HCID 67422397[1-(3-Bromo-benzyl)-3-[3-(3-methanesulfonylaminocarbonyl-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl esterYield 71%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl sulfonamide (25 mg, 0.26 mmol) in tert-butanol (2.5 ml) and dichloromethane (2.5 ml) at rt under N2 was added EDC (99 mg, 0.52 mmol), DMAP (44 mg, 0.36 mmol) and 3-(3-{3-(3-bromo-benzyl)-2-[tert-butoxycarbonylimino]-2,3-dihydro-benzoimidazol-1-yl}-propoxy)-benzoic acid (150 mg, 0.26 mmol). The reaction was stirred for 24 h and then diluted with EtOAc and washed with a solution of KHSO4. The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure to provide [1-(3-bromo-benzyl)-3-[3-(3-methanesulfonylaminocarbonyl-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-ylidene]-carbamic acid tert-butyl ester (120 mg, 71%). HPLC-MS 657, 659 [M+1]+.

Workup

  1. washwashed with a solution of KHSO4
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d0a1f96f4914334ac9e45c1f5e25323
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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