Sodium Hydroxide → HCID 117628654, compound

HRID 510199Notes

Reaction equation

HRID 510199 reaction equation
[CH3:1][CH:2]([CH3:33])[C@@H:3]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]([O:30]CC)=[O:29])[CH:26]=3)[NH:21][CH:20]=2)[CH:16]=[N:17][CH:18]=1)[C:4](=[O:11])[NH:5][CH2:6][C:7]([F:10])([F:9])[F:8].[OH-].[Na+]>CO>[CH3:1][CH:2]([CH3:33])[C@@H:3]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]([OH:30])=[O:29])[CH:26]=3)[NH:21][CH:20]=2)[CH:16]=[N:17][CH:18]=1)[C:4](=[O:11])[NH:5][CH2:6][C:7]([F:8])([F:10])[F:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 89495557HCID 89495557, compound

Product 1

HCID 117628654HCID 117628654, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To ethyl 3-(5-(3-methyl-1-oxo-1-(2,2,2-trifluoroethylamino)butan-2-ylamino)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate 3-1a (0.775 g, 1.724 mmol) in methanol (18 mL) was added sodium hydroxide (5.17 ml, 5.17 mmol). The mixture was heated at 50° C. for 18 hrs. The reaction was concentrated in vacuo and aqueous washed with diethyl ether. The aqueous extract was concentrated and 1N HCl added until a precipitate forms (˜pH6). The solid was filtered to give the desired product. 0.467 g. LRMS (ESI) m/z 436.2 [(M+H)+; calcd for C20H20F3N5O3: 436.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washaqueous washed with diethyl ether
  3. extractionThe aqueous extract
  4. concentrationwas concentrated
  5. addition1N HCl added until a precipitate forms (˜pH6)
  6. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-e72ff68a79974f538394765ff3da2b7a
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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