Triethylamine → HCID 118159855, compound

HRID 628405Notes

Reaction equation

HRID 628405 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:22]([CH3:25])=[N:23][N:24]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:14]=[C:15]([CH2:20]O)[CH:16]=[C:17]([Cl:19])[CH:18]=3)[C:6]=2[CH:7]=1.[CH2:26]([N:28](CC)[CH2:29][CH3:30])[CH3:27].CS(Cl)(=O)=O.N1CCCC1>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[C:3]2[N:4]([C:22]([CH3:25])=[N:23][N:24]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[N:8]([CH2:12][C:13]3[CH:14]=[C:15]([CH2:20][N:28]4[CH2:29][CH2:30][CH2:27][CH2:26]4)[CH:16]=[C:17]([Cl:19])[CH:18]=3)[C:6]=2[CH:7]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 31268PyrrolidineHCID 31297Methanesulfonyl chlorideHCID 118159441HCID 118159441, compound

Product 1

HCID 118159855HCID 118159855, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of {3-[(4-bromo-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)methyl]-5-chlorophenyl}methanol (0.360 g, 0.858 mmol, from Step 4) in DCM (50. mL) was treated with triethylamine (510 μL, 3.6 mmol) and methanesulfonyl chloride (220 μL, 2.9 mmol, Aldrich). After 30 minutes, the solvent was removed in vacuo, and the residue was dissolved in a mixture of THF (20. mL) and methanol (20. mL). The solution was added to a mixture of pyrrolidine (0.42 mL, 5 mmol, aldrich) and triethylamine (0.61 mL, 4.3 mmol) in THF (10 mL). The reaction was stirred for 1 hour, and then the solvent was removed in vacuo. The residue was partitioned between water and DCM. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-10% MeOH in DCM, was used to purify product. Yield: (0.30 g, 74%).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in a mixture of THF (20. mL) and methanol (20. mL)
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between water and DCM
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washFlash chromatography, eluting with a gradient from 0-10% MeOH in DCM
  9. customto purify product

Sources & evidence

ORD record
ord-09d29f6a37f24bb8a7882b44a6f6c954
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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