Sodium hydride → HCID 68382764, compound

HRID 603455Notes

Reaction equation

HRID 603455 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:20][CH2:19]3)=[N:9][CH:10]=1)#[N:4].[CH2:31](I)[CH2:32][CH3:33]>CN(C=O)C>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH2:31][CH2:32][CH3:33])[CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[C@H:21]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:20][CH2:19]3)=[N:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 68382772HCID 68382772, compound

Product 1

HCID 68382764HCID 68382764, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.08 g, 3.16 mmol) was added to a solution of ethyl ((1S)-5-{3-[(5-cyano-2-pyridinyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 264) (0.6 g, 1.58 mmol) in DMF (15 mL). The heterogeneous mixture was stirred at rt for 30 min. Propyl iodide (0.62 mL, 6.32 mmol) was added, and the mixture was stirred at rt for 18 h. The excess NaH was quenched by the addition of water (5 mL) and the aqueous phase extracted with Et2O. The combined Et2O extracts were washed with water and brine, then dried (MgSO4), filtered, and concentrated under reduced pressure. The product (0.63 g, 99%) was isolated after column chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD2Cl2) δ 8.35 (dd, 1H), 7.54 (dd, 1H), 7.06 (d, 1H), 6.78 (d, 1H), 6.69 (d, 1H), 6.52 (dd, 1H), 4.17 (q, 2H), 3.99 (t, 2H), 3.72 (t, 2H), 3.56-3.44 (m, 3H), 2.95-2.78 (m, 2H), 2.71 (dd, 1H), 2.46-2.35 (m, 2H), 2.12-2.05 (m, 2H), 1.72-1.58 (m, 3H), 1.28 (t, 3H), 0.96 (t, 3H).

Workup

  1. stirringthe mixture was stirred at rt for 18 h
  2. customThe excess NaH was quenched by the addition of water (5 mL)
  3. extractionthe aqueous phase extracted with Et2O
  4. washThe combined Et2O extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-228219c49db64b5da79f41c280143602
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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