Dimethylamine → HCID 59825008, compound

HRID 886571Notes

Reaction equation

HRID 886571 reaction equation
[OH:1][CH:2]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[CH:19][N:18]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:15]3=[N:16][CH:17]=2)[CH:11]=1)[C:3]([OH:5])=O.[CH:39]([N:42](C(C)C)[CH2:43]C)(C)C.[C:48](Cl)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50].CNC>ClCCl>[CH3:39][N:42]([CH3:43])[C:3]([CH:2]([O:1][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[CH:19][N:18]([S:29]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)(=[O:31])=[O:30])[C:15]3=[N:16][CH:17]=2)[CH:11]=1)=[O:5]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 59825043HCID 59825043, compound

Product 1

HCID 59825008HCID 59825008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Hydroxy-{5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-acetic acid (208 mg, 0.393 mmol) was dissolved in dichloromethane (3.0 mL) and cooled in an ice water bath. Di-iso-propylethylamine (137 μL, 0.786 mmol) and pivaloyl chloride (48.3 μL, 0.393 mmol) were added. After 10 minutes, dimethylamine solution (2 M tetrahydrofuran) was added (393 μL, 0.786 mmol) and the mixture was stirred for 15 h. The mixture was then diluted with dichloromethane and washed with saturated sodium bicarbonate (1×) and brine (1×), dried over sodium sulfate, filtered and concentrated to a foam (quantitative). The material was used as is in the next step. MS: m/z 641 (M+H+).

Workup

  1. temperaturecooled in an ice water bath
  2. washwashed with saturated sodium bicarbonate (1×) and brine (1×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a foam (quantitative)

Sources & evidence

ORD record
ord-05d694e7293646ee9491239baa5b6907
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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