Methanol → HCID 178426553, compound

HRID 1514886Notes

Reaction equation

HRID 1514886 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[NH:16][N:15]=[N:14][N:13]=2)[CH:7]=[C:6]([CH3:17])[C:3]=1[CH:4]=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=1[NH2:36])[C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH3:32])[CH:26]=1)=[O:23].C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].CO>CS(C)=O.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[CH3:32][C:27]1[CH:26]=[C:25]([NH:24][C:22]([C:21]2[CH:33]=[CH:34][C:35]3[N:36]=[C:4]([C:3]4[C:2]([CH3:1])=[CH:9][C:8]([O:10][CH2:11][C:12]5[NH:16][N:15]=[N:14][N:13]=5)=[CH:7][C:6]=4[CH3:17])[NH:18][C:19]=3[CH:20]=2)=[O:23])[CH:30]=[CH:29][C:28]=1[CH3:31]

Participants

7

Reactant 4

HCID 887MethanolHCID 2733225Ytterbium triflateHCID 66965643HCID 66965643, compoundHCID 178428967HCID 178428967, compound

Product 1

HCID 178426553HCID 178426553, compound

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2,6-dimethyl-4-(1H-tetrazol-5-yl-methoxy)-benzaldehyde (50 mg) in DMSO (1 mL) were added 3,4-diamino-N-(3,4-dimethyl-phenyl)-benzamide (55 mg), Yb(OTf)3 (13 mg), and Cu(OTf)2 (8 mg). The reaction mixture was stirred in open air at ambient temperature overnight. The mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to give 2-[2,6-dimethyl-4-(1H-tetrazol-5-yl-methoxy)-phenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethyl-phenyl)-amide: MS (m/z) 468.16 (M+1).

Workup

  1. extractionthe whole was loaded onto a solid phase extraction (SPE) cartridge that
  2. washWash-to-waste (5 mL MeOH)
  3. customby elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N)
  4. customafter evaporation of volatiles
  5. customthe crude was further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c706be9739d6457596663ff297b7d05a
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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