Epichlorohydrin → HCID 22508879, compound

HRID 2111769Notes

Reaction equation

[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:22])[C:19]([OH:21])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:23])[NH:6]2.[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:22])[C:19]([O:21][CH2:24][CH:26]4[CH2:27][O:28]4)=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:23])[NH:6]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-ol (Example 1), (200 mg, 0.64 mmol), epichlorohydrin (297 mg, 3.21 mmol) and potassium carbonate (445 mg, 3.21 mmol) in DMF (1 ml) was stirred at 50° C. for 6 h. After cooling to RT and concentration in vacuo the crude material was purified by chromatography on silica gel eluting with 50% ethyl acetate in hexanes to afford the title compound (190 mg, 81%) as a yellowish solid. MS: (M+H)+=369.

Workup

temperatureAfter cooling to RT
concentrationconcentration in vacuo the crude material
customwas purified by chromatography on silica gel eluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-a04e26d1afac4bc68f06bd4c32270653
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521450B2

Reaction notes

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