Dimethylformamide → HCID 22100652, compound

HRID 1458410Notes

Reaction equation

HRID 1458410 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[C:8]([O:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].BrC[C:37]1[CH:46]=[C:45]2[C:40]([CH:41]=[CH:42][C:43](C#N)=[CH:44]2)=[CH:39][CH:38]=1.[C:49](OCC)(=O)C.[CH3:55][N:56]([CH:58]=O)C>O>[CH3:1][C:2]1[N:6]([CH2:49][C:41]2[C:40]3[C:45](=[CH:46][CH:37]=[CH:38][CH:39]=3)[C:44]([C:55]#[N:56])=[CH:43][CH:42]=2)[C:5]2[CH:7]=[C:8]([O:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])=[CH:10][C:4]=2[N:3]=1.[CH3:1][C:2]1[N:3]([CH2:49][C:41]2[C:40]3[C:45](=[CH:46][CH:37]=[CH:38][CH:39]=3)[C:44]([C:58]#[N:56])=[CH:43][CH:42]=2)[C:4]2[CH:10]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])[C:8]([O:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]3)=[CH:7][C:5]=2[N:6]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 98377487-(Bromomethyl)-2-naphthonitrileHCID 22100646HCID 22100646, compound

Product 2

HCID 22100652HCID 22100652, compoundHCID 22100801HCID 22100801, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-methyl-5-(tert-butyldimethylsilyl)oxy-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)benzimidazole (6.6 g) in DMF (50 mL) was added NaH (0.65 g) at ambient temperature. After stirring at ambient temperature for 30 minutes 7-bromomethyl-2-naphthonitrile (3.88 g) was added. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction was worked up between ethyl acetate and H2O. The organic layer was dried, concentrated and purified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient) to afford 2-methyl-5-(tert-butyldimethylsilyl)oxy-6-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole and 2-methyl-6-(tert-butyldimethylsilyl)oxy-5-(N-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyanonaphth-1-yl)methylbenzimidazole.

Workup

  1. additionwas added
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate/CH2Cl2 /methanol, gradient)

Sources & evidence

ORD record
ord-eaa836c89893413a8a9e64d460481503
Source dataset
uspto-grants-1998_12
Patent number
US05849759

Reaction notes

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