Water → HCID 178449976, compound

HRID 1262214Notes

Reaction equation

[OH-:1].[Na+].O.[C:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[N:26]3[C:21]([CH:22]=[N:23][C:24](S(C)(=O)=O)=[N:25]3)=[CH:20][CH:19]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)(=O)C>[C:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[N:26]3[C:21]([CH:22]=[N:23][C:24]([OH:1])=[N:25]3)=[CH:20][CH:19]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

Conditions

Temperature: 120 °C

Procedure

10 M sodium hydroxide in water (2.74 mL, 52.4 mmol) was heated at 100° C. N-tert-butyl-3-(2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (780 mg, 1.91 mmol) was added portion wise over 10 minutes. The reaction mixture was heated at 120° C. for 60 minutes and then cooled to room temperature. Glacial acetic acid was added to adjust the pH to 4 and the mixture was stirred at room temperature for 30 minutes. The solid was filtered and washed sequentially with water (75 mL) and Et2O (50 mL) to obtain N-tert-butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide as a red-orange solid (460 mg, 70%). LCMS (m/e) 347 (M+H); 1H-NMR (d6-DMSO, 400 MHz) δ 9.00 (s, 1H), 8.68 (s, 1H), 8.47 (d, 1H, J=8.0 Hz), 7.78 (d, 1H, J=7.7 Hz), 7.71-7.64 (m, 1H), 7.59 (s, 1H), 7.30 (d, 1H, J=4.8 Hz), 7.01 (d, 1H, J=4.8 Hz), 1.91 (s, 1H), 1.13 (s, 9H).

Workup

temperaturecooled to room temperature
filtrationThe solid was filtered
washwashed sequentially with water (75 mL) and Et2O (50 mL)

Sources & evidence

ORD record: ord-b0102799d4e34eca869c96c416841433
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

Loading…