Hydrochloric Acid → 5-Hydroxy-6-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-nicotinonitrile

HRID 1483734

反応式

HRID 1483734 の反応式
[OH:1][B:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][C:12]3[C:19]([O:20]COC)=[CH:18][C:15]([C:16]#[N:17])=[CH:14][N:13]=3)=[CH:10][C:5]=2[CH2:4][O:3]1.Cl.CCOCC>CO>[OH:20][C:19]1[C:12]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[B:2]([OH:1])[O:3][CH2:4][C:5]=3[CH:10]=2)=[N:13][CH:14]=[C:15]([CH:18]=1)[C:16]#[N:17]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 674396606-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-5-methoxymethoxy-nicotinonitrile

生成物 1

HCID 674398705-Hydroxy-6-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-nicotinonitrile収率 41.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
65 °C

実験手順

To a suspension of 6-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-5-yloxy)-5-methoxymethoxy-nicotinonitrile (0.28 g, 0.89 mmol) in methanol (4 mL) was added 1 M HCl in ether (1.79 mL, 1.79 mmol) at 0° C. The reaction was heated at 65° C. for 2 hours. Methanol was removed under reduced pressure and the product was purified by reverse phase prep HPLC using CH3CN/H2O (0.1% AcOH) as the eluent to yield the title compound (0.10 g, 41%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.22 (s, 1H), 8.02 (s, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.57 (s, 1H), 7.19 (s, 1H), 7.15-7.09 (m, 1H), 4.98 (s, 2H); MS (ES) m/z: 267 (M−1)−; HPLC purity 92.91% (Maxplot), 92.41% (220 nm).

後処理

  1. customMethanol was removed under reduced pressure
  2. customthe product was purified by reverse phase prep HPLC

出典と根拠

ORDレコード
ord-8d546b633f844fbea895097426926f6a
出典データセット
uspto-grants-2016_08
特許番号
US09416146B2

関連ノート

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