Sodium Hydroxide → HCID 136199031, compound

HRID 1854342Notes

Reaction equation

HRID 1854342 reaction equation
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]2=[N:7][CH:8]=1)[NH2:2].[O:22]1[CH2:27][CH2:26][CH:25]([CH:28]=O)[CH2:24][CH2:23]1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[OH-].[Na+]>CO.C(Cl)Cl>[O:22]1[CH2:27][CH2:26][CH:25]([C:28]2[N:4]3[C:5]4[CH:11]=[CH:10][NH:9][C:6]=4[N:7]=[CH:8][C:3]3=[N:1][N:2]=2)[CH2:24][CH2:23]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 12217721Iodo benzene diacetateHCID 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

Product 1

HCID 136199031HCID 136199031, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.100 g, 0.330 mmol, Preparation #9) in MeOH (2 mL) was added tetrahydro-2H-pyran-4-carbaldehyde (0.038 g, 0.330 mmol, J&W PharmLab) in DCM (1 mL). The reaction mixture was stirred at ambient temperature for about 2 h before iodobenzene diacetate (0.106 g, 0.330 mmol) was added. The reaction mixture was stirred at ambient temperature for about 15 min before it was concentrated to constant weight. To the residue was added MeOH (2 mL) followed by aqueous NaOH (2 N, 0.330 mL, 0.659 mmol). The reaction mixture was heated at about 60° C. for about 1 h. The crude reaction mixture was purified by RP-HPLC (Table 2, Method f). The combined product-containing fractions were concentrated under reduced pressure to remove MeCN and then lyophilized to afford 1-(tetrahydro-2H-pyran-4-yl)-6H-pyrrolo[2,3-e][1, 2, 4]triazolo[4,3-a]pyrazine as a white solid (0.028 g, 35%): LC/MS (Table 2, Method a) Rt=1.25 min; MS m/z: 244 (M+H)+.

Workup

  1. additionwas added
  2. concentrationwas concentrated to constant weight
  3. additionTo the residue was added MeOH (2 mL)
  4. temperatureThe reaction mixture was heated at about 60° C. for about 1 h
  5. customThe crude reaction mixture
  6. customwas purified by RP-HPLC (Table 2, Method f)
  7. additionThe combined product-containing fractions
  8. concentrationwere concentrated under reduced pressure
  9. customto remove MeCN

Sources & evidence

ORD record
ord-cfed204e2f3940b2b9e7b5cfc27db888
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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