2-Hydroxyacetohydrazide → HCID 86683643, compound

HRID 1509262Notes

Reaction equation

[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:20][C:21]4[NH:26][C:25](=S)[CH2:24][O:23][C:22]=4[N:28]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH:36][CH2:37][C:38]([NH:40][NH2:41])=O>CC1C=CC(C)=CC=1>[OH:36][CH2:37][C:38]1[N:26]2[C:21]3[CH:20]=[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:18]([C:15]4[CH:16]=[CH:17][C:12]([C:8]5([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][CH2:10][CH2:9]5)=[CH:13][CH:14]=4)=[N:28][C:22]=3[O:23][CH2:24][C:25]2=[N:41][N:40]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of tert-butyl(1-(4-(7-phenyl-2-thioxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (250 mg, 0.513 mmol) and 2-hydroxyacetohydrazide (230 mg, 2.56 mmol) in p-xylene (1.5 ml) was heated to 150° C. for 30 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 20% ethyl acetate in n-hexanes) to give the title compound (40 mg, 15%). LCMS (Method D): RT=1.297 min, M+1=526. 1H NMR (500 MHz, CDCl3) δ 8.33 (1H, s), 7.37-7.32 (2H, m), 7.31-7.27 (5H, m), 7.25-7.20 (2H, m), 5.59 (2H, s), 5.06 (2H, bs), 5.02 (1H, bs), 2.53-2.43 (4H, m), 2.14-2.02 (1H, m), 1.88-1.76 (1H, m), 1.45-1.27 (9H, bs).

Workup

customThe resulting reaction mixture
concentrationwas concentrated to dryness under reduced pressure
custompurified by Biotage silica gel chromatography (gradient 0% to 20% ethyl acetate in n-hexanes)

Sources & evidence

ORD record: ord-dcc26d9210514791aa285c389063004a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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