2-(Dimethylamino)ethanol → HCID 11250074, compound

HRID 2105523Notes

Reaction equation

HRID 2105523 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][OH:6])[CH3:3].[H-].[Na+].Cl[C:10]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([N:31]4[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=5[NH:33][C:32]4=[O:40])[CH2:27][CH2:26]3)=[CH:20][CH:19]=2)[C:15]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:14][C:11]=1[C:12]#[N:13]>CS(C)=O.O>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][C:10]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([N:31]4[C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=5[NH:33][C:32]4=[O:40])[CH2:29][CH2:30]3)=[CH:20][CH:19]=2)[C:15]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 114098042-Chloro-6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl]-5-phenylnicotinonitrile

Product 1

HCID 11250074HCID 11250074, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N,N dimethylaminoethanol in DMSO (1 mL) was added NaH (60% dispersion in mineral oil, 0.019 g, 0.481 mmol). The mixture was heated to 50° C. for 15 min. After cooling, 2-Chloro-6-(4-{[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]methyl}phenyl]-5-phenylnicotinonitrile (2-6, 0.050 g, 0.096 mmol) was added and the reaction was allowed to stir for 16 hr at rt. The resulting mixture was diluted with water (10 mL) and the resulting precipitate was filtered. The filtered cake was purified by reverse phase HPLC. (5% CH3CN: 95% H2O+0.01% TFA to 95% CH3CN: 5% H2O+0.01% TFA). 1H-NMR (500 MHz, d6 DMSO) δ 10.93 (s, 1H), 9.86 (bs, 2H), 8.45 (s, 1H), 7.40-7.55 (m, 4H), 7.25-7.40 (m, 6H), 7.00 (d, J=2.93, 3H), 4.85 (t, J=4.89, 2H), 4.45 -4.55 (m, 1H), 4.34 (s, 2H), 3.64 (bs, 2H), 3.46 (d, J=11.72, 2H), 3.10-3.25 (m, 2H), 2.94 (d, J=4.15, 6H), 2.56-2.69 (m, 2H), 1.93, (d, J=12.00, 2H). HRMS m/z (M+H) Calcd: 573.2973, found: 573.2957.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered
  3. customThe filtered cake was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-823548a5fd254f3ebcb3e25efbc0c8f8
Source dataset
uspto-grants-2009_08
Patent number
US07579355B2

Reaction notes

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