Isoniazid → HCID 86683659, compound

HRID 1509291Notes

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][N:40]=[CH:39][CH:38]=1>CC1C=CC(C)=CC=1>[C:29]1([C:19]2[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:8]4([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:11][CH2:10][CH2:9]4)=[CH:13][CH:14]=3)=[N:28][C:22]3[O:23][CH2:24][C:25]4[N:26]([C:36]([C:37]5[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=5)=[N:44][N:45]=4)[C:21]=3[CH:20]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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 isonicotinic acid hydrazide (127 mg, 0.923 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-hexanes) to give the title compound (14 mg, 12%), LCMS (Method A): RT=6.28 min, M+1=573. 1H NMR (500 MHz, CDCl3): 8.90 (2H, d), 7.70 (2H, d), 7.38 (1H, s), 7.36-7.32 (2H, d), 7.31-7.27 (2H, d), 7.25-7.18 (3H, m), 6.98-6.93 (2H, dd), 5.66 (2H, s), 2.55-2.41 (4H, m), 2.14-2.01 (1H, m), 1.88-1.78 (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-hexanes)

Sources & evidence

ORD record: ord-45ebd8dc811440d184b44551ad7354e6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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