Trimethyl orthoacetate → HCID 86683594, compound

HRID 1509181Notes

Reaction equation

[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:20][C:21]4[NH:26]/[C:25](=[N:27]/[NH2:28])/[CH2:24][O:23][C:22]=4[N:29]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CO[C:39](OC)(OC)[CH3:40]>>[CH3:39][C:40]1[N:26]2[C:21]3[CH:20]=[C:19]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:8]5([NH:7][C:6](=[O:36])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:11][CH2:10][CH2:9]5)=[CH:17][CH:16]=4)=[N:29][C:22]=3[O:23][CH2:24][C:25]2=[N:27][N:28]=1

Participants

Reactant 2

HCID 15050Trimethyl orthoacetate

HCID 178452593HCID 178452593, compound

Product 1

HCID 86683594HCID 86683594, compoundYield 47%

Procedure

A solution of (E)-tert-butyl(1-(4-(2-hydrazono-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.103 mmol) in 1,1,1-trimethoxyethane (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 100% ethyl acetate in n-hexanes) to give the title compound (24 mg, 47%). LCMS (Method A): RT=6.71 min, M+1=510. 1H NMR (500 MHz, CDCl3): 7.84 (1H, s), 7.37-7.33 (5H, m), 7.30-7.27 (2H, m), 7.24-7.19 (2H, m), 5.59 (2H, s), 2.87 (3H, s), 2.54-2.40 (4H, m), 2.13-2.02 (1H, m), 1.87-1.78 (1H, m), 1.45-1.27 (9H, br s).

Workup

customThe resulting reaction mixture
concentrationwas concentrated to dryness under reduced pressure
custompurified by Biotage silica gel chromatography (gradient 0% to 100% ethyl acetate in n-hexanes)

Sources & evidence

ORD record: ord-09d4d135fc044001a2cfa85318beeeae
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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