Water → 1-(4-acetylphenyl)-8-{[(2-chloropyridin-3-yl)carbonyl]amino}-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide

HRID 968132Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:34]=[CH:33][C:14]3[CH2:15][CH2:16][C:17]4[C:18]([C:30]([NH2:32])=[O:31])=[N:19][N:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]#[CH:29])=[CH:24][CH:23]=5)[C:21]=4[C:13]=3[CH:12]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[OH:36]S(C(F)(F)F)(=O)=O.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:28]([C:25]1[CH:26]=[CH:27][C:22]([N:20]2[C:21]3[C:13]4[CH:12]=[C:11]([NH:10][C:8]([C:7]5[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=5)=[O:9])[CH:34]=[CH:33][C:14]=4[CH2:15][CH2:16][C:17]=3[C:18]([C:30]([NH2:32])=[O:31])=[N:19]2)=[CH:23][CH:24]=1)(=[O:36])[CH3:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 8-{[(2-chloropyridin-3-yl)carbonyl]amino}-1-(4-ethynylphenyl)-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide (442 mg, 1.2 mmol), water (65 mg, 3.6 mmol), and triflic acid (270 mg, 1.8 mmol) in dioxane (10 mL) was heated to 100° C. for 18 h. The mixture was cooled to RT, aqueous NaHCO3 was added, and filtered. The product was washed with water and ether, and dried. This gave product (293 mg, 67%). 1H NMR was consistent with its structure.

Workup

temperatureThe mixture was cooled to RT
filtrationfiltered
washThe product was washed with water and ether
customdried

Sources & evidence

ORD record: ord-f0cf18bd920b45d3b141dc7dd8c1146b
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06956052B2

Reaction notes

Loading…