6-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-one → HCID 57554502, compound

HRID 551950Notes

Reaction equation

HRID 551950 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[NH2:21][C:22]1[CH:23]=[CH:24][C:25]2[O:30][C:29]([CH3:32])([CH3:31])[O:28][C:27](=[O:33])[C:26]=2[CH:34]=1>>[CH3:31][C:29]1([CH3:32])[O:30][C:25]2[CH:24]=[CH:23][C:22]([NH:21][CH2:15][C:14]3[CH:17]=[CH:18][C:11]([C:10]#[C:9][C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:19])[F:1])=[CH:4][CH:5]=4)=[CH:12][CH:13]=3)=[CH:34][C:26]=2[C:27](=[O:33])[O:28]1

Participants

3

Reactant 2

HCID 116153306-Amino-2,2-dimethyl-benzo[1,3]dioxin-4-oneHCID 85781067HCID 85781067, compound

Product 1

HCID 57554502HCID 57554502, compoundYield 30%

Procedure

The title compound was prepared following procedure described in example 1, step c) from 4-{[4-(trifluoromethyl)phenyl]ethynyl}benzaldehyde (1.22 g; 4.43 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) and 6-amino-2,2-dimethyl-benzo[1,3]dioxin-4-one (855 mg; 4.43 mmol). Purification of the crude (2.6g) by precipitation in DCM upon addition of pentane gave 590 mg (30%) of the title compound as a brown solid. HPLC, Rt: 4.76 min (purity: 76.2%). LC/MS, M+(ESI): 452, M−(ESI): 450.1, 1H NMR (CDCl3) δ 7.59 (s, 4H), 7.51 (d, J=7.5 Hz, 2H), 7.34 (d, J=7.7 Hz, 2H), 7.15 (s, 1H), 6.80 (m, 2H), 4.34 (s, 2H), 1.68 (s, 6H). Purification of the filtrate by flash chromatography on silicagel (EtOAc/c-Hex 10:90 then 20:80) gave another 420 mg of the title compound (21%) as a yellow powder.

Workup

  1. customThe title compound was prepared following procedure
  2. customPurification of the crude (2.6g)
  3. customby precipitation in DCM
  4. additionupon addition of pentane

Sources & evidence

ORD record
ord-f9731a7eceb2437cb8f04036a3d6c348
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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