Hydrogen Peroxide → HCID 58557819, compound

HRID 1969789Notes

Reaction equation

HRID 1969789 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([C@@H:26]2[C@H:30]([CH2:31][CH3:32])[CH2:29][C@H:28]([NH:33][S:34]([CH:37]3[CH2:39][CH2:38]3)(=[O:36])=[O:35])[CH2:27]2)[N:7]2[C:12]3[CH:13]=[CH:14][N:15](S(C4C=CC(C)=CC=4)(=O)=O)[C:11]=3[N:10]=[CH:9][C:8]=12)[CH:2]=[CH2:3].B.CSC.[OH:44]O.[OH-].[Na+]>C1COCC1.O.CCOC(C)=O>[CH2:31]([C@H:30]1[C@@H:26]([C:6]2[N:7]3[C:12]4[CH:13]=[CH:14][NH:15][C:11]=4[N:10]=[CH:9][C:8]3=[C:4]([CH2:1][CH2:2][CH2:3][OH:44])[N:5]=2)[CH2:27][C@@H:28]([NH:33][S:34]([CH:37]2[CH2:39][CH2:38]2)(=[O:35])=[O:36])[CH2:29]1)[CH3:32]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboron2×HCID 67999341HCID 67999341, compound

Product 1

HCID 58557819HCID 58557819, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-((1S,3S,4R)-3-(3-allyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)-4-ethylcyclopentyl)cyclopropanesulfonamide (0.090 g, 0.16 mmol, prepared using H with Preparation #12, Preparation #Z.1, HATU and DIEA, and Q with Lawesson's reagent and mercury (II) trifluoroacetate) in THF (3 mL) at about 0° C. was added BH3•DMS (2 M in THF, 0.040 mL, 0.079 mmol). After about 2 h, additional BH3•DMS (2 M in THF, 0.040 mL, 0.079 mmol) was added to the reaction mixture. After about 6 h total, a premixed solution of H2O2 (30% aqueous, 0.324 mL, 3.17 mmol) and NaOH (2 N aqueous, 0.793 mL, 1.58 mmol) was added to the reaction mixture. After stirring for about 15 h, EtOAc (20 mL) and water (20 mL) were added to the reaction mixture. The organic layer was separated, washed with brine (20 mL), and concd in vacuo. The crude residue was purified by chromatography on silica gel (12 g) eluting with EtOAc to provide N-((1S,3R,4S)-3-ethyl-4-(3-(3-hydroxypropyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)cyclopentyl)cyclopropanesulfonamide (0.025 g, 37%) as a white solid: LC/MS (Table 1, Method a) Rt=1.70 min; MS m/z: 432 (M+H)+.

Workup

  1. waitAfter about 6 h total
  2. customThe organic layer was separated
  3. washwashed with brine (20 mL), and concd in vacuo
  4. customThe crude residue was purified by chromatography on silica gel (12 g)
  5. washeluting with EtOAc

Sources & evidence

ORD record
ord-ff7b363cdedd42dd8b89f5d5ee58fd10
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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