Ethanol → HCID 24887569, compound

HRID 914786Notes

Reaction equation

HRID 914786 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:25])[C:19](C(O)(C)C)=[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]([CH3:26])[NH:6]2.[CH2:27]1[O:29][CH:28]1[CH2:30][OH:31].C(N(CC)CC)C.C([OH:41])C>>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:25])[C:19]([O:29][CH2:27][C@@H:28]([OH:41])[CH2:30][OH:31])=[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]([CH3:26])[NH:6]2

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 11164GlycidolHCID 223379962-{4-[(4-Fluoro-2-methyl-1H-indol-5-yl)oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl}propan-2-ol

Product 1

HCID 24887569HCID 24887569, compoundYield 48%

Procedure

A mixture of Example 1 (45 mg, 0.14 mmol), S-(−) glycidol (330 mg, 4.2 mmol ) and triethylamine (5 μL) in ethanol (15 mL) was heated at 75° C. for 2 h. The reaction was concentrated in vacuo. The crude material was purified by chromatography on silica gel eluting with 100% ethyl acetate to provide the title compound (26 mg, 48% yield) as a white solid. MS: (M+H)+=387.2

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe crude material was purified by chromatography on silica gel eluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-7d34a819b1c74b22b5b7d4cd4e7c1d57
Source dataset
uspto-grants-2007_09
Patent number
US07265113B2

Reaction notes

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