Sodium Acetate → HCID 90403137, compound

HRID 589810Notes

Reaction equation

HRID 589810 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[C:12]([N:32]=1)=[N:13][CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:19][CH:18]=1)[CH:16]=2.[C:33]([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CN(C=O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH3:33])=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[C:12]([N:32]=1)=[N:13][CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:19][CH:18]=1)[CH:16]=2

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 90403682HCID 90403682, compound

Product 1

HCID 90403137HCID 90403137, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In a 40 ml vial 4-fluoro-3-(6-(4-(2-morpholinoethoxy)phenyl)oxazolo[4,5-b]pyridin-2-yl)aniline I-23 (15 mg, 0.032 mmol, 1.0 eq.) was dissolved in DCE. Paraformadelhyde (30 mg) followed by sodium acetate (2.62 mg, 0.032 mmol, 1.0 eq) was added and reaction was heated for one hour. Sodium triacetoxy borohydride (16 mg, 0.08 mmol, 2.5 eq) was added and the reaction was heated to 80° C. for 4 hours. LCMS indicated that the reaction was complete with a formation of new peak of desired mass 449.2 (M+1). The reaction was concentrated under reduced pressure. The crude reaction was dissolved in DMF and filtered through a frit funnel to remove the insoluble matter. The clear filtrate by purified by HPLC to get the desired product 4-fluoro-N-methyl-3-(6-(4-(2-morpholinoethoxy)phenyl)oxazolo[4,5-b]pyridin-2-yl)aniline (Example 421). The TFA salt was neutralized by passing a methanolic solution of the compound through a bicarbonate resin. MS M/Z=449.2 (M+1). RT=1.33: Method B.

Workup

  1. additionwas added
  2. customreaction
  3. temperaturewas heated for one hour
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customThe crude reaction
  6. filtrationfiltered through a frit funnel
  7. customto remove the insoluble matter
  8. customThe clear filtrate by purified by HPLC

Sources & evidence

ORD record
ord-9c30e69a656144dabde733b9c3912109
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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