Water → HCID 66965569, compound

HRID 1515005Notes

Reaction equation

HRID 1515005 reaction equation
[CH3:1][C:2]1([CH3:19])[O:6][C@H:5]([CH2:7][O:8][C:9]2[CH:16]=[C:15]([CH3:17])[C:12]([CH:13]=O)=[C:11]([CH3:18])[CH:10]=2)[CH2:4][O:3]1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][C:37]=1[NH2:38])[C:24]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=1)=[O:25].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].O>CS(C)=O.CCOC(C)=O>[CH3:34][C:29]1[CH:28]=[C:27]([NH:26][C:24]([C:23]2[CH:35]=[CH:36][C:37]3[N:38]=[C:13]([C:12]4[C:15]([CH3:17])=[CH:16][C:9]([O:8][CH2:7][C@@H:5]5[CH2:4][O:3][C:2]([CH3:19])([CH3:1])[O:6]5)=[CH:10][C:11]=4[CH3:18])[NH:20][C:21]=3[CH:22]=2)=[O:25])[CH:32]=[CH:31][C:30]=1[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 2733225Ytterbium triflateHCID 66965643HCID 66965643, compoundHCID 86651273HCID 86651273, compound

Product 1

HCID 66965569HCID 66965569, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2,6-dimethylbenzaldehyde (145 mg, 0.55 mmol) and 3,4-diamino-N-(3,4-dimethylphenyl)-benzamide (153 mg, 0.55 mmol) in DMSO (8 mL) was added Yb(OTf)3 (68 mg, 0.11 mmol) and the mixture was stirred at ambient temperature overnight. The reaction mixture was partioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, brine, dried with MgSO4, filtered and concentrated. Purification by flash chromatography using heptane/EtOAc (1:2) as eluent gave 2-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2,6-dimethylphenyl]-3H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a pale yellow solid 1H NMR (Methanol-d4, 400 MHz): δ 8.30 (d, 1H), 7.90 (d, 1H), 7.77 (dd, 1H), 7.47 (s, 1H), 7.44 (dd, 1H), 7.13 (d, 1H), 6.79 (s, 2H), 4.51 (m, 1H), 4.19 (q, 1H), 4.07 (d, 2H), 3.91 (q, 1H), 2.29 (s, 3H), 2.26 (s, 3H), 2.15 (s, 6H), 1.44 (s, 3H), 1.38 (s, 3H). MS (m/z) 500.3 (M+1); Retention time: 1.51 min (Method 10).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-397dc93136ae4ce8bb08e064531eda26
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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