Hexane → HCID 19783387, compound

HRID 257520Notes

Reaction equation

HRID 257520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][C:9]2[C:10]([N:15]=1)=[N:11][CH:12]=[CH:13][CH:14]=2.CCCCCC.[H-].[Na+].Br[CH2:25][C:26]1[CH:43]=[CH:42][C:29]([C:30]([N:32]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH:33]([CH3:35])[CH3:34])=[O:31])=[CH:28][C:27]=1[O:44][CH3:45]>CC(N(C)C)=O>[CH:36]1([N:32]([CH:33]([CH3:35])[CH3:34])[C:30](=[O:31])[C:29]2[CH:42]=[CH:43][C:26]([CH2:25][N:11]3[CH:12]=[CH:13][CH:14]=[C:9]4[N:8]=[C:7]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=5)[N:15]=[C:10]34)=[C:27]([O:44][CH3:45])[CH:28]=2)[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 6612277HCID 6612277, compoundHCID 9999080HCID 9999080, compound

Product 1

HCID 19783387HCID 19783387, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-(2-Pyridyl)-1H-imidazo(4,5-b)pyridine (1.1 g, 5.6 mmol) was added portionwise with stirring over 5 minutes to a suspension of hexane-washed NaH (150 mg, 6.16 mmol) in dimethylacetamide (15 ml) under Ar and stirred at room temperature for 1 hour. 4-Bromomethyl-3-methoxy-N-cyclohexyl-N-isopropylbenzamide (2.1 g, 5.6 mmol) was added portionwise over 30 minutes and the mixture was stirred overnight at 25° C. The solvent was removed at <50° C. in vacuo using an oil pump and the residue was chromatographed on silica gel with 95/5/1 CH2Cl2 /MeOH/NH4OH to give the titled product (1.95 g, 67%) as a glass. Anal. Calcd. for C29H33N5O2.H2O: C, 69.44; H, 7.03; N, 13.96. Found: C, 69.70; H, 7.16; N, 13.87.

Workup

  1. stirringthe mixture was stirred overnight at 25° C
  2. customThe solvent was removed at <50° C. in vacuo
  3. customthe residue was chromatographed on silica gel with 95/5/1 CH2Cl2 /MeOH/NH4OH

Sources & evidence

ORD record
ord-2f0f705eb04448f4ae88fa853b1debb4
Source dataset
uspto-grants-1993_11
Patent number
US05262426

Reaction notes

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