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m-Chloroperbenzoic acid → N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-methylpropane-2-sulfonamide

HRID 1969558
Notes
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Reaction equation

HRID 1969558 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([NH2:30])[CH2:4]1)[CH3:2].CCN(C(C)C)C(C)C.[CH3:40][C:41]([S:44](Cl)=[O:45])([CH3:43])[CH3:42].ClC1C=CC=C(C(OO)=[O:55])C=1>C(Cl)Cl.CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=5)(=[O:22])=[O:21])[C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C@@H:5]([NH:30][S:44]([C:41]([CH3:43])([CH3:42])[CH3:40])(=[O:45])=[O:55])[CH2:4]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 46868612-Methylpropane-2-sulfinyl chlorideHCID 58557840(1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine

Product 1

HCID 67998018N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-methylpropane-2-sulfonamide
Yield 64.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of (1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanamine (115 mg, 0.271 mmol, Preparation #BB.1*) in DCM (1.5 mL) was added DIEA (0.071 mL, 0.406 mmol) followed by 2-methylpropane-2-sulfinic chloride (0.037 mL, 0.298 mmol). After about 4 h the reaction mixture was diluted with EtOAc (10 mL) and aqueous saturated NaHCO3 (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered and concd in vacuo. The crude residue was dissolved in DCM (1.5 mL) and a freshly prepared solution of m-chloroperbenzoic acid (0.271 mL, 0.271 mmol, 1M in DCM) was added. After about 2 h the reaction mixture was diluted with EtOAc (10 mL) and saturated aqueous NaHCO3 (10 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered and concd in vacuo. The crude residue was purified by chromatography on silica gel eluting with EtOAc to provide N-((1S,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl)-2-methylpropane-2-sulfonamide (95 mg, 64% yield) as an oil. LC/MS (Table 1, Method a) Rt=2.40 min; MS m/z: 545 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. dissolutionThe crude residue was dissolved in DCM (1.5 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customThe crude residue was purified by chromatography on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-28f7a148ef014d7b9789005d4e39f179
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426411B2

Reaction notes

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