Diketene → n-[1-Acetyl-3-(acetylamino)-1h-indazol-5-yl]-3-oxobutanamide

HRID 227697Notes

Reaction equation

[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[C:6]([NH:14][C:15](=[O:17])[CH3:16])=[N:5]1)(=[O:3])[CH3:2].[CH2:18]=[C:19]1[O:23][C:21](=[O:22])[CH2:20]1>C(#N)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH:13][C:21](=[O:22])[CH2:20][C:19](=[O:23])[CH3:18])=[CH:10][CH:11]=2)[C:6]([NH:14][C:15](=[O:17])[CH3:16])=[N:5]1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

The product from Step (c) above (2.6 g, 11.4 mmol) was dissolved in acetonitrile (20 mL) and diketene (0.86 mL, 11.2 mmol) was added in portions over min, then the solution was sealed and heated to 50° C. overnight. The reaction mixture was then cooled, filtered and the filtrate was concentrated to give the title compound as a dark tan solid (2.6 g, 73%). NMR 1H NMR (400 MHz, DMSO-D6) δ 10.86 (s, 1H), 10.32 (s, 1H), 8.25-8.20 (m, 2H), 7.75 (dd, J=8.9, 2.0, 1H), 3.59 (s, 2H), 2.63 (s, 3H), 2.22 (s, 3H), 3.18 (s, 3H) MS m/z 317.0 [M+H]+

Workup

customthe solution was sealed
temperatureThe reaction mixture was then cooled
filtrationfiltered
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-b2a492bcb7a64109900683c493ab1e72
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560467B2

Reaction notes

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