Ethanolamine → HCID 118159455, compound

HRID 628275Notes

Reaction equation

HRID 628275 reaction equation
C(N(C(C)C)CC)(C)C.CS(OS(C)(=O)=O)(=O)=O.[CH3:19][C:20]1[N:24]2[C:25]3[CH:31]=[C:30]([CH3:32])[N:29]([CH2:33][C:34]4[CH:35]=[C:36]([CH2:40]O)[CH:37]=[CH:38][CH:39]=4)[C:26]=3[CH:27]=[CH:28][C:23]2=[N:22][N:21]=1.S([O-])(=O)(=O)C.[CH2:47]([CH2:49][NH2:50])[OH:48]>C(Cl)Cl.C1COCC1.CO>[CH3:19][C:20]1[N:24]2[C:25]3[CH:31]=[C:30]([CH3:32])[N:29]([CH2:33][C:34]4[CH:35]=[C:36]([CH:37]=[CH:38][CH:39]=4)[CH2:40][NH:50][CH2:49][CH2:47][OH:48])[C:26]=3[CH:27]=[CH:28][C:23]2=[N:22][N:21]=1

Participants

9

Reactant 5

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 85257MethanesulfonateHCID 118159565HCID 118159565, compound

Product 1

HCID 118159455HCID 118159455, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (26 μL, 0.15 mmol) and methanesulphonic anhydride (13 mg, 0.073 mmol, Aldrich) were added to a solution of {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 Step 1) in DCM (1.0 mL). The mixture was stirred until mesylate formation was determined complete as judged by LCMS, and the mixture was then concentrated. The residue was re-dissolved in a mixture of THF (0.50 mL) and MeOH (0.50 mL) and ethanolamine (12 μL, 0.20 mmol, Aldrich) was added and the reaction was stirred for 1.5 hours. The crude reaction mixture was purified using preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (8.5 mg, 50%).

Workup

  1. concentrationthe mixture was then concentrated
  2. additionwas added
  3. customThe crude reaction mixture
  4. customwas purified
  5. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (8.5 mg, 50%)

Sources & evidence

ORD record
ord-6a4c2a21096541a682569a7cad0b1bf9
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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