Sodium hydride → HCID 178440453, compound

HRID 1898422Notes

Reaction equation

HRID 1898422 reaction equation
[OH:1][N:2]=[C:3]([NH2:7])[CH:4]([CH3:6])[CH3:5].[H-].[Na+].[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[NH:18][C:19]1[NH:23][C:22]2[C:24]3[CH2:25][C:26]([CH3:36])([CH3:35])[O:27][C:28]=3[C:29]([C:31](OC)=O)=[CH:30][C:21]=2[N:20]=1>C1COCC1.O>[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:12]=1[NH:18][C:19]1[NH:23][C:22]2[C:24]3[CH2:25][C:26]([CH3:36])([CH3:35])[O:27][C:28]=3[C:29]([C:31]3[O:1][N:2]=[C:3]([CH:4]([CH3:6])[CH3:5])[N:7]=3)=[CH:30][C:21]=2[N:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 178496994HCID 178496994, compound

Product 1

HCID 178440453HCID 178440453, compoundYield 17.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, to a solution of N′-hydroxyisobutyrimidamide (0.028 g, 0.268 mmol) in THF was added sodium hydride (0.021 g, 0.51 mmol). The reaction mass was refluxed for 15-20 minutes. Then added methyl 2-((2-chloro-6-fluorophenyl)amino)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (Step-1 of Intermediate-15, 0.100 g, 0.255 mmol) and continued reflux for 4-5 h. The reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified column chromatography to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.28 (d, 6H), 1.48 (s, 6H), 3.09 (m, 3H), 7.24 (m, 1H), 7.39 (m, 1H), 7.54 (d, J=7.2 Hz, 1H), 9-10 (s, 1H), 10.5 (s, 1H); MS [M]+: 458.14.

Workup

  1. temperatureThe reaction mass was refluxed for 15-20 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe obtained crude
  6. customwas purified column chromatography

Sources & evidence

ORD record
ord-aea21a62744e4265bea8823bbd89f603
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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