Methanol → HCID 67194147, compound

HRID 1259372Notes

Reaction equation

HRID 1259372 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29](C3(CC=C)CC3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:42][CH2:41]C1.[CH3:46]O.[CH2:48]1[CH2:52][O:51][CH2:50][CH2:49]1>O.C(Cl)(Cl)Cl.O=[Os](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH:28][S:29]([C:49]3([CH2:48][CH:52]([OH:51])[CH2:41][OH:42])[CH2:46][CH2:50]3)(=[O:31])=[O:30])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 67195451HCID 67195451, compound

Product 1

HCID 67194147HCID 67194147, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

OsO4 (0.1 mg, 0.00002 mol) was added to a stirred solution of 8-(1-allyl-cyclopropanesulfonylamino)-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (120 mg, 0.0002 mol) and N-methylmorpholine-N-oxide (35 mg, 0.0003 mol) in water and THF (3 mL). The resulting mixture was stirred at room temperature for 12 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and water. The organic layer was concentrated to afford 75 mg of the crude product which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and water
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-41dace090a6c4a49a9c227a80ece2dcb
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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