HCID 178452595, compound → HCID 86683632, compound

HRID 1509243Notes

Reaction equation

HRID 1509243 reaction equation
[C:1]([O:5][C:6](=[O:41])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:20][C:21]4[NH:26]/[C:25](=[N:27]/[NH:28][C:29](=O)[CH:30]([F:32])[F:31])/[CH2:24][O:23][C:22]=4[N:34]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CC1C=CC(C)=CC=1>[F:31][CH:30]([F:32])[C:29]1[N:26]2[C:21]3[CH:20]=[C:19]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH:7][C:6](=[O:41])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)=[N:34][C:22]=3[O:23][CH2:24][C:25]2=[N:27][N:28]=1

Participants

3

Reactant 1

HCID 178452595HCID 178452595, compound

Product 1

HCID 86683632HCID 86683632, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A solution of (E)-tert-butyl(1-(4-(2-(2-(2,2-difluoroacetyl)hydrazono)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (80 mg, 0.142 mmol) in p-xylene (1 ml) was heated to 150° C. for 15 minutes under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure and purified by Biotage silica gel chromatography (gradient 0% to 2% methanol in dichloromethane) to give the title compound (15 mg, 20%). LCMS (Method D): RT=1.529 min, M+1=546.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated to dryness under reduced pressure
  3. custompurified by Biotage silica gel chromatography (gradient 0% to 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-126b501c08f54a72a7fc78c4757df47d
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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