Cyclopropanecarbohydrazide → HCID 86683647, compound

HRID 1509266Notes

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].[CH:36]1([C:39]([NH:41][NH2:42])=O)[CH2:38][CH2:37]1>CC1C=CC(C)=CC=1>[CH:36]1([C:39]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:42][N:41]=2)[CH2:38][CH2:37]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 (150 mg, 0.308 mmol) and cyclopropanecarbohydrazide (41 mg, 0.410 mmol) in p-xylene (1.5 ml) was heated to 150° C. for 20 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 (36 mg, 32%). LCMS (Method D): RT=1.457 min, M+1=536.

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-ce1f733434fc4a93835859866cca5d97
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221838B2

Reaction notes

Loading…