2-(Dimethylamino)ethanol → HCID 136436926, compound

HRID 990233Notes

Reaction equation

HRID 990233 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:29])[C:13]3[C:14](=[C:16]([CH2:26][CH2:27][CH3:28])[N:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH3:40])[CH2:35][CH2:34]2)(=[O:32])=[O:31])=[CH:6][N:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:51][N:52](C)[CH2:53]CO>O>[CH3:51][N:52]([CH3:53])[CH2:2][CH2:1][O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:29])[C:13]3[C:14](=[C:16]([CH2:26][CH2:27][CH3:28])[N:17]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=4)[N:18]=3)[N:15]=2)=[CH:8][C:7]([S:30]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39][CH3:40])[CH2:35][CH2:34]2)(=[O:31])=[O:32])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135485687HCID 135485687, compound

Product 1

HCID 136436926HCID 136436926, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of the title compound of Example 26 (200 mg, 0.35 mmol), potassium bis(trimethylsilyl)amide (352 mg, 1.76 mmol) and 2-dimethylaminoethanol (1.5 ml) was stirred at 90° C. for 18 hours, then allowed to cool. Water (5 ml) was added, the mixture extracted with ethyl acetate (3×5 ml) and the combined extracts dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (95:5 to 90:10), to give the title compound (147 mg, 68%) as an off-white foam. Found: C, 56.35; H, 6.37; N, 20.12. C29H39N9O4S; 0.50H2O requires C, 56.29; H, 6.52; N, 20.37%. δ (CDCl3): 0.94 (3H, t), 1.04 (3H, t), 1.72 (2H, m), 2.43 (8H, m), 2.56 (4H, m), 2.74 (2H, t), 2.95 (2H, t), 3.15 (4H, m), 4.80 (2H, t), 5.67 (2H, s), 7.07 (1H, d), 7.21 (1H, m), 7.61 (1H. m), 8.56 (1H, d), 8.62 (1H, s), 8.75 (1H, s), 12.23 (1H, s). LRMS: m/z 610 (M+1)+.

Workup

  1. temperatureto cool
  2. extractionthe mixture extracted with ethyl acetate (3×5 ml)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5eec0c4e4f7941c18d43dec6f32498df
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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