Sodium hydride → HCID 86717564, compound

HRID 712112Notes

Reaction equation

HRID 712112 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[OH:14][CH2:15][C:16]1([N:23]2[C:27]3=[C:28]4[S:34][CH:33]=[CH:32][C:29]4=[N:30][CH:31]=[C:26]3[N:25]=[CH:24]2)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1>O1CCCC1.CN(C)C=O>[OH:14][CH2:15][C:16]1([N:23]2[C:27]3=[C:28]4[S:34][CH:33]=[CH:32][C:29]4=[N:30][CH:31]=[C:26]3[N:25]=[CH:24]2)[CH2:21][CH2:20][C:19](=[CH:3][C:1]#[N:2])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 86717563HCID 86717563, compound

Product 1

HCID 86717564HCID 86717564, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl cyanomethylphosphonate (38.6 mg, 0.218 mmol) in tetrahydrofuran (0.5 mL) stirring at about 0° C. was added sodium hydride (10.5 mg, 0.262 mmol). To this was added a solution of 4-(hydroxymethyl)-4-(1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)cyclohexanone (56 mg, 0.18 mmol) in N,N-dimethylformamide (0.45 mL). The mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water, causing formation of solids. The solids were filtered to give 18 mg of pure desired product. The filtrate was diluted with EtOAc, washed with water, and concentrated to give an additional 39 mg of the crude product. LCMS calculated for C17H17N4OS (M+H)+: m/z=325.1. Found: 325.0. 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 8.15 (s, 1H), 7.47 (d, J=5.6 Hz, 1H), 7.18 (d, J=5.6 Hz, 1H), 5.20 (s, 1H), 4.34 (s, 2H), 2.80 (d, J=4.0 Hz, 3H), 2.59-2.29 (m, 4H), 1.26 (d, J=15.3 Hz, 2H) ppm.

Workup

  1. customThe reaction was quenched with water
  2. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-da969f6a83de40a9972dcef38638aaf9
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…