2-(Dimethylamino)ethanol → HCID 58486118, compound

HRID 655335Notes

Reaction equation

HRID 655335 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24].O[C:27]1[CH:28]=[N:29][C:30]([C:33]2[CH:34]=[C:35]([CH:48]=[CH:49][CH:50]=2)[CH2:36][N:37]2[C:41]3=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=[C:40]3[O:39][C:38]2=[O:47])=[N:31][CH:32]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][O:24][C:27]1[CH:32]=[N:31][C:30]([C:33]2[CH:34]=[C:35]([CH:48]=[CH:49][CH:50]=2)[CH2:36][N:37]2[C:41]3=[N:42][C:43]([CH3:46])=[CH:44][CH:45]=[C:40]3[O:39][C:38]2=[O:47])=[N:29][CH:28]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanol2×HCID 11776Triphenylphosphine3×HCID 97268Di-tert-butyl azodicarboxylate3×HCID 58486100HCID 58486100, compound

Product 1

HCID 58486118HCID 58486118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.3 mmol) of polymer-bound triphenylphosphine (3 mmol/g) and 30 μl (0.3 mmol) of 2-dimethylaminoethanol are added successively to a suspension of 67 mg (0.2 mmol) of 3-[3-(5-hydroxypyrimidin-2-yl)benzyl]-5-methyl-3H-oxazolo[4,5-b]pyridin-2-one in 3 ml of DMF. 69 mg (0.30 mmol) of di-tert-butyl azodicarboxylate are subsequently added. The reaction mixture is shaken at room temperature for 18 hours. A further 100 mg (0.3 mmol) of polymer-bound triphenylphosphine (3 mmol/g) and 69 mg (0.30 mmol) of di-tert-butyl azodicarboxylate are added, and the mixture is shaken at room temperature for 18 h. A further 100 mg (0.3 mmol) of polymer-bound triphenylphosphine (3 mmol/g), 69 mg (0.30 mmol) of di-tert-butyl azodicarboxylate and 30 μl (0.3 mmol) of 2-dimethylaminoethanol are subsequently added, and the mixture is shaken at room temperature for 18 h. The reaction mixture is filtered, the filtrate is evaporated in vacuo, and the residue is purified by column chromatography on silica gel, giving “A109”. The crude product is purified by preparative HPLC; ESI: 406; HPLC: Rt=2.31 min (method B);

Workup

  1. stirringthe mixture is shaken at room temperature for 18 h
  2. stirringthe mixture is shaken at room temperature for 18 h
  3. filtrationThe reaction mixture is filtered
  4. customthe filtrate is evaporated in vacuo
  5. customthe residue is purified by column chromatography on silica gel
  6. customgiving “A109”
  7. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-47b42fae22dd48729600e5d1d5b4f255
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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