Methyl morpholine oxide → (R)-4-(1-cyclopropylethylamino)-6-(3-(1,2-dihydroxyethyl)phenyl)pyrrolo[1,2-b]-pyridazine-3-carboxamide

HRID 1507958Notes

Reaction equation

HRID 1507958 reaction equation
[CH:1]1([C@H:4]([NH:6][C:7]2[C:8]3[N:9]([CH:16]=[C:17]([C:19]4[CH:24]=CC=C(C=C)[CH:20]=4)[CH:18]=3)[N:10]=[CH:11][C:12]=2[C:13]([NH2:15])=O)[CH3:5])[CH2:3][CH2:2]1.C[N+]1([O-])CC[O:31][CH2:30]C1.[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1.[OH2:40]>[Os](=O)(=O)(=O)=O.O>[CH:1]1([CH:4]([NH:6][C:7]2[C:8]3[N:9]([CH:16]=[C:17]([C:19]4[CH:24]=[CH:37][CH:36]=[C:35]([C@@H:39]([OH:38])[CH2:30][OH:31])[CH:20]=4)[CH:18]=3)[N:10]=[CH:11][C:12]=2[C:13]([NH2:15])=[O:40])[CH3:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 68291702(R)-4-(1-cyclopropylethylamino)-6-(3-vinylphenyl)pyrrolo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 68291169(R)-4-(1-cyclopropylethylamino)-6-(3-(1,2-dihydroxyethyl)phenyl)pyrrolo[1,2-b]-pyridazine-3-carboxamideYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 30318Osmium TetroxideCatalyst

Conditions

Temperature
23 °C

Procedure

To a solution of (R)-4-(1-cyclopropylethylamino)-6-(3-vinylphenyl)pyrrolo[1,2-b]pyridazine-3-carboxamide (54.7 mg, 0.158 mmol) in THF/water (4/1) (Volume: 2 mL) at 0° C. were added 4-methylmorpholine N-oxide (0.082 mL, 0.395 mmol) and osmium tetroxide 4% in water (0.039 mL, 6.32 μmol). The reaction mixture was warmed up to 23° C. and stirred for 16 hrs. The reaction mixture was purified on Preparative HPLC (Method A) to yield the desired product (32.2 mg, 41% yield). MS (ES+) m/z: 381.2 (M+H); HPLC: 100%, retention time: 2.836 min (analytical HPLC Method B).

Workup

  1. customThe reaction mixture was purified on Preparative HPLC (Method A)

Sources & evidence

ORD record
ord-3c20747bddec442081910812dabfaa29
Source dataset
uspto-grants-2015_12
Patent number
US09221826B2

Reaction notes

Loading…