Tetrahydrofuran → HCID 118159587, compound

HRID 628269Notes

Reaction equation

HRID 628269 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:16](OCC)=[O:17])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.C1COCC1.[Li+].[BH4-]>CO>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:16][OH:17])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydride2×HCID 118177559HCID 118177559, compound

Product 1

HCID 118159587HCID 118159587, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl (1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)(phenyl)acetate (0.008 g, 0.02 mmol, from Step 1) was dissolved in MeOH (0.5 mL) and THF (0.5 mL) and LiBH4 (0.0025 g, 0.10 mmol, 90% purity, Aldrich) was added. The reaction was stirred for 4 hours and additional LiBH4 (0.006 g, 0.25 mmol) was added and the reaction continued for a further 3 hours. The reaction was quenched by the addition of water and diluted with MeCN, filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (5 mg, 70%).

Workup

  1. waitthe reaction continued for a further 3 hours
  2. customThe reaction was quenched by the addition of water
  3. additiondiluted with MeCN
  4. filtrationfiltered
  5. custompurified by preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (5 mg, 70%)

Sources & evidence

ORD record
ord-19e7f0ad89ae483ea156f6d8a7513738
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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