Benzoylhydrazine → HCID 86683668, compound

HRID 1509302Notes

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].[C:36]([NH:44][NH2:45])(=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CC1C=CC(C)=CC=1>[C:37]1([C:36]2[N:26]3[C:21]4[CH:20]=[C:19]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[C:18]([C:15]5[CH:16]=[CH:17][C:12]([C:8]6([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][CH2:10][CH2:9]6)=[CH:13][CH:14]=5)=[N:28][C:22]=4[O:23][CH2:24][C:25]3=[N:45][N:44]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=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 (100 mg, 0.205 mmol) and benzoic acid hydrazide (84 mg, 0.615 mmol) in p-xylene (2 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 20% ethyl acetate in n-hexane) to give the title compound (46 mg, 40%). LCMS (Method D): RT=1.546 min, M+1=572. 1H NMR (500 MHz, CDCl3): 7.77-7.69 (2H, m), 7.64-7.57 (2H, m), 7.56-7.50 (1H, t), 7.49-7.41 (2H, t), 7.34-7.30 (2H, m), 7.28 (1H, s), 7.22-7.14 (3H, m), 6.95-6.90 (2H, dd), 5.65 (2H, s), 2.55-2.40 (3H, m), 2.15-2.01 (2H, m), 1.89-1.77 (1H, m), 1.46-1.24 (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-hexane)

Sources & evidence

ORD record: ord-a6239624d470497b8c9e4fc66a1e31bb
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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