Methanol → HCID 25229636, compound

HRID 1967476Notes

Reaction equation

HRID 1967476 reaction equation
N1C=CC=CC=1C([O:9][CH:10]1[C:14]2=[N:15][C:16]3[C:17](=[N:18][CH:19]=[C:20]([NH:22][C:23]([C:25]4[N:26]([CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=5)[C:27]5[C:32]([CH:33]=4)=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=5)=[O:24])[CH:21]=3)[N:13]2[CH2:12][CH2:11]1)=O.CO>C(Cl)(Cl)Cl.ClCCl.N.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[OH:9][CH:10]1[C:14]2=[N:15][C:16]3[C:17](=[N:18][CH:19]=[C:20]([NH:22][C:23]([C:25]4[N:26]([CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=5)[C:27]5[C:32]([CH:33]=4)=[CH:31][C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][CH:28]=5)=[O:24])[CH:21]=3)[N:13]2[CH2:12][CH2:11]1

Participants

7

Reactant 2

HCID 887MethanolHCID 66905102HCID 66905102, compound

Product 1

HCID 25229636HCID 25229636, compound

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 222AmmoniaSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.065 g (0.07 mmol) of 3-[[[1-(3-fluorobenzyl)-5-trifluoromethyl-1H-indol-2-yl]carbonyl]amino]-7,8-dihydro-6H-pyrrolo[2′,1′:2,3]imidazo[4,5-b]pyridin-6-yl pyridine-2-carboxylate, prepared in Example 8.1, in 10 ml of chloroform is admixed with 0.022 g (0.7 mmol) of methanol and 0.0127 g (0.07 mmol) of copper acetate. After seven hours of stirring at ambient temperature, the reaction mixture is diluted with 10 ml of dichloromethane and 10 ml of aqueous ammonia, with stirring. The organic phase is separated, washed with 10 ml of water, dried over sodium sulfate and concentrated under reduced pressure. The resulting product is subsequently purified by successive chromatography on a silica column and then on a neutral alumina column. This gives 0.012 g of the expected product.

Workup

  1. stirringwith stirring
  2. customThe organic phase is separated
  3. washwashed with 10 ml of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting product is subsequently purified by successive chromatography on a silica column

Sources & evidence

ORD record
ord-db5b0771d3e94775b1bf3c9263c19609
Source dataset
uspto-grants-2013_04
Patent number
US08420817B2

Reaction notes

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