Hydrochloric Acid → HCID 46216494, compound

HRID 2367222Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To N-{6-[2-amino-6-(methyloxy)-4-pyrimidinyl]-1H-indazol-3-yl}acetamide (115 mg, 0.218 mmol) in CH3OH (20 mL) was added HCl (0.21 mL, 2.5 mmol, 12 M), and the reaction mixture was stirred for 12 hours at 60° C. The reaction was cooled to room temperature and stirred over the weekend. The mixture was concentrated, and the resulting yellow solid was purified on a Gilson RPHPLC(CH3CN/H2O w/0.1% TFA). The fractions containing the desired product were combined and concentrated. The resulting yellow solid was dissolved in water and treated with NaOH (1M). The resulting pink solid was filtered to afford the title compound (15 mg, 25%). LC-MS (ES) m/z=257 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 3.86 (s, 3H), 5.40 (s, 2H), 6.58 (s, 1H), 6.64 (s, 2H), 7.54 (dd, J=8.6, 1.0 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H), 7.95 (s, 1H), 11.57 (s, 1H).

Workup

temperatureThe reaction was cooled to room temperature
stirringstirred over the weekend
concentrationThe mixture was concentrated
customthe resulting yellow solid was purified on a Gilson RPHPLC(CH3CN/H2O w/0.1% TFA)
additionThe fractions containing the desired product
concentrationconcentrated
dissolutionThe resulting yellow solid was dissolved in water
additiontreated with NaOH (1M)
filtrationThe resulting pink solid was filtered

Sources & evidence

ORD record: ord-f0bbfd55f6854c9eb36734fb0ee82ccd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

Loading…