Tetrahydrofuran → 2-amino-3-fluoro-N-prop-2-ynyl-benzamide

HRID 1041424Notes

Reaction equation

HRID 1041424 reaction equation
[F:1][C:2]1[C:7]2[NH:8]C(=O)O[C:11](=[O:12])[C:6]=2[CH:5]=[CH:4][CH:3]=1.O1CCCC1.[CH2:19]([NH2:22])[C:20]#[CH:21]>>[NH2:8][C:7]1[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=1[C:11]([NH:22][CH2:19][C:20]#[CH:21])=[O:12]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 239041PropargylamineHCID 105353938-Fluoroisatoic anhydride

Product 1

HCID 815106892-amino-3-fluoro-N-prop-2-ynyl-benzamideYield 79%

Procedure

8-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione (3.00 g, 16.6 mmol) was dissolved in tetrahydrofuran (100 mL, 1.23 mol) and prop-2-ynylamine (1.70 mL, 24.8 mmol) was added. The reaction was stirred for 2 hours and then concentrated under reduced pressure onto silica gel. Purification by silica gel chromatography (dry loaded) using a gradient of 0-60% EtOAc/hex as the eluting solvent to obtain 2-amino-3-fluoro-N-prop-2-ynyl-benzamide as a white solid (2.52 g, 79%). m.p.=89-91° C.; LCMS (m/e) 138 (M-NHCH2CCH); 1H-NMR (CDCl3, 400 MHz) δ 7.14 (d, 1H, J=8.0 Hz), 7.12-7.05 (m, 1H), 6.64-6.56 (m, 1H), 6.28-6.14 (m, 1H), 5.67 (bs, 2H), 4.27-4.19 (m, 2H), 2.34-2.27 (m, 1H).

Workup

  1. concentrationconcentrated under reduced pressure onto silica gel
  2. customPurification
  3. customby silica gel chromatography (dry loaded)

Sources & evidence

ORD record
ord-b921b479b71e446382f0c9eb086b5063
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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