Dichloromethane → HCID 67216960, compound

HRID 1969534Notes

Reaction equation

HRID 1969534 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([C:26]23[CH2:33][CH2:32][C:29]([NH:34][S:35]([CH:38]4[CH2:40][CH2:39]4)(=[O:37])=[O:36])([CH2:30][CH2:31]2)[CH2:28][CH2:27]3)[N:7]2[C:12]3[CH:13]=[CH:14][N:15]([S:16]([C:19]4[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=4)(=[O:18])=[O:17])[C:11]=3[N:10]=[CH:9][C:8]=12)C=C.C[N+]1([O-])CCOCC1.C(Cl)Cl.[O:52]1[CH2:57][CH2:56][O:55]CC1>O.[Os](=O)(=O)(=O)=O>[OH:52][CH:57]([CH2:56][OH:55])[CH2:1][C:4]1[N:5]=[C:6]([C:26]23[CH2:31][CH2:30][C:29]([NH:34][S:35]([CH:38]4[CH2:40][CH2:39]4)(=[O:36])=[O:37])([CH2:28][CH2:27]2)[CH2:32][CH2:33]3)[N:7]2[C:12]3[CH:13]=[CH:14][N:15]([S:16]([C:19]4[CH:20]=[CH:21][C:22]([CH3:23])=[CH:24][CH:25]=4)(=[O:17])=[O:18])[C:11]=3[N:10]=[CH:9][C:8]=12

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 82029Methyl morpholine oxideHCID 67999139HCID 67999139, compound

Product 1

HCID 67216960HCID 67216960, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of N-(4-(3-allyl-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo-[2.2.2]octan-1-yl)cyclopropanesulfonamide (0.27 g, 0.47 mmol, prepared using E with 4-(tert-butoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylic acid [Prime Organics], K with cyclopropylsulfonyl chloride, H from Preparation #12, HATU and DIEA, Q with Lawesson's reagent and mercury (II) trifluoroacetate) in 1,4-dioxane (10 mL) and water (1 mL) was added N-methylmorpholine-N-oxide (0.22 g, 1.8 mmol) followed by osmium tetroxide (4 wt % in water, 0.36 mL, 0.047 mmol). The reaction mixture was stirred for about 15 h and then DCM (20 mL) and water (10 mL) were added to the reaction mixture. The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel eluting with 10-50% MeCN in DCM, to provide N-(4-(3-(2,3-dihydroxypropyl)-6-tosyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)bicyclo[2.2.2]octan-1-yl)cyclopropanesulfonamide (0.009 g, 3%): LC/MS (Table 1, Method a) Rt=1.90 min; MS m/z: 612 (M−H)−.

Workup

  1. customThe organic layer was separated
  2. customconcd in vacuo, and purified by chromatography on silica gel eluting with 10-50% MeCN in DCM

Sources & evidence

ORD record
ord-83a2fc346ecf405c87a4f1fc76d67d53
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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