2-Methylpropanehydrazide → HCID 86683649, compound

HRID 1509269Notes

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:41][NH2:42])(=O)[CH:37]([CH3:39])[CH3:38]>CC1C=CC(C)=CC=1>[CH:37]([C:36]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:42][N:41]=1)([CH3:39])[CH3:38]

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 (150 mg, 0.308 mmol) and isobutyrohydrazide (28 mg, 0.308 mmol) in p-xylene (1.5 ml) was heated to 150° C. for 15 minutes under microwave irradiation. The resulting reaction mixture was concentrated to dryness under reduced pressure. The crude residue was purified by Biotage silica gel chromatography (gradient 0% to 20% ethyl acetate in n-hexanes) to give the title compound (28 mg, 17%). LCMS (Method D): RT=1.497 min, M+1=538. 1H NMR (500 MHz, CDCl3) δ 7.85 (1H, s), 7.36-7.31 (5H, m), 7.28 (2H, m), 7.24-7.19 (2H, m), 5.56 (2H, s), 3.46-3.36 (1H, m), 2.57-2.39 (4H, m), 2.13-2.02 (1H, m), 1.88-1.76 (1H, m), 1.57-1.53 (6H, d), 1.44-1.29 (9H, bs).

Workup

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

Sources & evidence

ORD record: ord-f4370389efa744b6be19b97962672bce
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

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