Water → HCID 178482109, compound

HRID 1262303Notes

Reaction equation

[OH-:1].[Na+].O.CS([C:7]1[N:12]=[CH:11][C:10]2=[CH:13][CH:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]2[N:8]=1)=O>C(O)(=O)C>[OH:1][C:7]1[N:12]=[CH:11][C:10]2=[CH:13][CH:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]2[N:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 8-dram vial, 19.10 M of Sodium hydroxide in Water (7.88 mL, 1.50E2 mmol) and Water (7.88 mL, 438 mmol) water were added. The mixture was heated at 100° C. N-[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide (2.00 g, 5.49 mmol) was added portion wise over 10 minutes. The reaction mixture was heated at 120° C. for 60 minutes. HPLC suggested no SM. The reaction was cooled to room temperature. Glacial acetic acid was added to adjust pH to 4. The mixture was stirred at room temperature for 30 minutes. The solid was filtered, washed with water and subsequently with Et2O. The resulting solid was dried under vacuum overnight to give N-[2-(2-Hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenyl]-N-methyl-methanesulfonamide as a yellow solid (1.60 g, 92%).

Workup

temperatureThe reaction mixture was heated at 120° C. for 60 minutes
temperatureThe reaction was cooled to room temperature
filtrationThe solid was filtered
washwashed with water and subsequently with Et2O
customThe resulting solid was dried under vacuum overnight

Sources & evidence

ORD record: ord-9e1a1812f2204c83a9c47bb9f7715615
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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