Pyrrolidine → HCID 118159698, compound

HRID 628278Notes

Reaction equation

HRID 628278 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH2:22]O)[CH:19]=[CH:20][CH:21]=4)[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[CH:24]([N:27]([CH:30]([CH3:32])C)CC)([CH3:26])C.CS(OS(C)(=O)=O)(=O)=O.S([O-])(=O)(=O)C.N1CCCC1>C(Cl)Cl>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:27]5[CH2:24][CH2:26][CH2:32][CH2:30]5)[CH:17]=4)[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 85257MethanesulfonateHCID 118159565HCID 118159565, compound

Product 1

HCID 118159698HCID 118159698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To {3-[(1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)methyl]phenyl}methanol (15 mg, 0.049 mmol, from Example 36, Step 1) in DCM (1.0 mL) was added diisopropylethylamine (26 μL, 0.15 mmol) followed by methanesulphonic anhydride (17 mg, 0.098 mmol). After mesylate formation was determined to be complete as judged by LCMS, solvent was removed in vacuo and the residue was re-dissolved in a mixture of THF (0.50 mL) and methanol (0.50 mL). Pyrrolidine (0.016 mL, 0.20 mmol, Aldrich) was added and the reaction was stirred for 2.5 hours. The product was purified using preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (11.4 mg, 65%).

Workup

  1. customwas removed in vacuo
  2. dissolutionthe residue was re-dissolved in a mixture of THF (0.50 mL) and methanol (0.50 mL)
  3. customThe product was purified
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (11.4 mg, 65%)

Sources & evidence

ORD record
ord-f28795e83e3e436e9998a0342a2359c4
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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