Water → HCID 118159763, compound

HRID 628388Notes

Reaction equation

HRID 628388 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[N:22]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:60]=[C:61]([Cl:63])[CH:62]=2)[CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:40]([CH3:43])=[N:41][N:42]=4)[C:34]=3[CH:33]=[C:32]2[C:44]([O:46]CC2C=C(Cl)C=C(CN3CCC3)C=2)=[O:45])[CH2:25][CH2:24][CH2:23]1.[OH-].[Na+].O.CC#N>C1COCC1.CO>[N:22]1([CH2:26][C:27]2[CH:28]=[C:29]([CH:60]=[C:61]([Cl:63])[CH:62]=2)[CH2:30][N:31]2[C:35]3[CH:36]=[CH:37][C:38]4[N:39]([C:40]([CH3:43])=[N:41][N:42]=4)[C:34]=3[CH:33]=[C:32]2[C:44]([OH:46])=[O:45])[CH2:25][CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 131735351HCID 131735351, compound

Product 1

HCID 118159763HCID 118159763, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-(Azetidin-1-ylmethyl)-5-chlorobenzyl 6-[3-(azetidin-1-ylmethyl)-5-chlorobenzyl]-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylate trifluoroacetate salt (0.080 g, 0.085 mmol, from Step 8) in THF (2 mL) was treated with 1.0 M solution of NaOH in water (2 mL, 2 mmol). After 1 hour, MeCN and MeOH were added to make the reaction monophasic, and the product was purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH). Yield: (35 mg, 100%).

Workup

  1. customwas purified by preparative HPLC-MS (Waters XBridge C18
  2. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-b7581ae74cc648ffb92e18a18aeeb75d
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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