Dimethylamine, hydrochloride → 4-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acid

HRID 628896ノート

反応式

HRID 628896 の反応式
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1.[NH:22]([CH3:24])[CH3:23].Cl.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:3]=1

参加物

5

反応物 3

HCID 10473Dimethylamine, hydrochlorideHCID 81531DiisopropylethylamineHCID 56961213HCID 56961213、化合物2 回

生成物 1

HCID 569593354-(4-(Dimethylamino)-6-hydroxyquinolin-2-yl)benzoic acid収率 32.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

30 mg of 4-(4-fluoro-6-hydroxyquinolin-2-yl)benzoic acid (Compound 26) was mixed with 1 mmol Me2NH.HCl and 0.5 ml DIEA in 3 ml DMF and heated to 160° C. for 30 minutes. The solvent was evaporated to dryness and water was added. The solid was filtered and washed with water and dried. The crude was triturated with acetone to obtain 10.5 mg of Compound 47. 1H NMR (DMSO-d6 300 MHz TMS): δ 13.2 (b, 1H), 10.28 (s, 1H), 8.22 (m, 2H), 8.11 (d, 1H), 7.99 (d, 1H), 7.50 (s, 1H), 7.39 (d, 1H), 7.26 (s, 1H), 3.24 (s, 6H), MS (ESI): m/z=309.30 [M+1]+.

後処理

  1. customThe solvent was evaporated to dryness and water
  2. additionwas added
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude was triturated with acetone

出典と根拠

ORDレコード
ord-62ee1ed0053e4f3a8daf13184fea5c97
出典データセット
uspto-grants-2016_04
特許番号
US09315462B2

反応ノート

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