Phosphorus oxychloride → 4-Chloro-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 347573Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[N:20]([CH:21]=3)[N:19]=[CH:18][N:17]=[C:16]4O)[CH:10]=[CH:9][N:8]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:25]>C1(C)C=CC=CC=1.CN(C=O)C>[Cl:25][C:16]1[C:15]2=[CH:14][C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[CH:12]=3)=[CH:21][N:20]2[N:19]=[CH:18][N:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-ol (110 mg, 0.37 mmol) in toluene (100 mL) were added one drop of DMF and POCl3 (30 mL). The flask was sealed and heated at 100° C. for 3 d. The reaction mixture was cooled to rt and concentrated in vacuo. The residue was then dissolved in DCM, neutralized with saturated aq. NaHCO3 solution and the organic layer was separated. The aqueous layer was extracted with DCM (2×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product, which was used directly in the next step. MS(ESI) m/z 316.2/318.2 (M+H)+.

Workup

customThe flask was sealed
temperatureThe reaction mixture was cooled to rt
concentrationconcentrated in vacuo
dissolutionThe residue was then dissolved in DCM
customthe organic layer was separated
extractionThe aqueous layer was extracted with DCM (2×50 mL)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-20d6f167cd25466f80cd9c50b4d5ccd2
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173031B2

Reaction notes

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