Dimethylamine → HCID 58382209, compound

HRID 1628077Notes

Reaction equation

HRID 1628077 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.C1N=[CH:35][N:34]([C:37](N2C=NC=C2)=[O:38])[CH:33]=1.CCN(C(C)C)C(C)C.CNC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:37](=[O:38])[N:34]([CH3:35])[CH3:33])[N:20]=[C:15]2[CH:14]=1

Participants

6

Reactant 4

HCID 674Dimethylamine3×HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 58009787HCID 58009787, compound

Product 1

HCID 58382209HCID 58382209, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.413 g, 0.944 mmol, Preparation #1.1), CDI (0.184 g, 1.13 mmol), DIEA (0.412 mL, 2.36 mmol) and THF (10 mL). The mixture was allowed to stir at rt for about 1 h. Dimethylamine (2.0 M in THF, 0.472 mL, 0.944 mmol) was added to the mixture. After about 4 h, additional dimethylamine (2.0 M in THF, 0.236 mL, 0.472 mmol) was added. After about 12 h, dimethylamine (2.0 M in THF, 0.236 mL, 0.472 mmol) was added. After about 8 h, the mixture was concentrated under reduced pressure and the residue was dissolved in DCM (10 mL). The organic solution was then washed with water (2×4 mL). The organic layer was dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 0 to 10% MeOH/DCM to give 3-((6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)-1,1-dimethylurea (0.114 g, 24%): LC/MS (Table 2, Method b) Rt=2.62 min; MS m/z 509 (M+H)+.

Workup

  1. waitAfter about 4 h
  2. waitAfter about 12 h
  3. waitAfter about 8 h
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in DCM (10 mL)
  6. washThe organic solution was then washed with water (2×4 mL)
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 0 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-c37b89be428e43bb8196adf711cf9b61
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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