Dimethylamine → HCID 68526654, compound

HRID 2246551Notes

Reaction equation

HRID 2246551 reaction equation
[CH2:1]([C:3]1([OH:36])[C:8]2[CH:9]=[C:10]3[N:18]([C:19](=[O:20])[C:7]=2[CH2:6][O:5][C:4]1=[O:35])[CH2:17][C:16]1[C:15]([CH2:21][CH2:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][C:26]([OH:28])=O)=[C:14]2[CH:31]=[CH:32][CH:33]=[CH:34][C:13]2=[N:12][C:11]3=1)[CH3:2].Cl.[CH3:38][N:39](C)[CH2:40]CCN=C=NCC.ON1C2C=CC=CC=2N=N1.CNC.C(N(C(C)C)CC)(C)C>>[CH2:1]([C:3]1([OH:36])[C:8]2[CH:9]=[C:10]3[N:18]([C:19](=[O:20])[C:7]=2[CH2:6][O:5][C:4]1=[O:35])[CH2:17][C:16]1[C:15]([CH2:21][CH2:22][Si:23]([CH3:30])([CH3:29])[CH2:24][CH2:25][C:26]([N:39]([CH3:40])[CH3:38])=[O:28])=[C:14]2[CH:31]=[CH:32][CH:33]=[CH:34][C:13]2=[N:12][C:11]3=1)[CH3:2]

Participants

6

Reactant 5

HCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68530165HCID 68530165, compound

Product 1

HCID 68526654HCID 68526654, compound

Procedure

To a solution of Compound 47 (1 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19 mg, 0.099 mmol) and 1-hydroxybenzotriazole (catalytic amount). Dimethylamine (0.04 ml, M=2 in tetrahydrofuran) and diisopropylethylamine (0.1 ml) were added to the above solution at ice bath. The resulted solution was stirred at room temperature for 3 days. The reaction was quenched with 1 N HCl and extracted with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate, filtrated through silica gel, and concentrated by rotary evaporation. Purification by radial preparative-layer chromatography (ethyl acetate/hexanes 50/50 to methanol/chloroform 2/98) provided 12 mg of Compound 48 as a yellow solid.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltrated through silica gel
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by radial preparative-layer chromatography (ethyl acetate/hexanes 50/50 to methanol/chloroform 2/98)

Sources & evidence

ORD record
ord-3de7abf0b95e4367827bfc0e5354eedf
Source dataset
uspto-grants-2010_03
Patent number
US07687496B2

Reaction notes

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