Ethanol → HCID 178434683、化合物

HRID 1505000ノート

反応式

HRID 1505000 の反応式
[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([F:22])[F:21])[N:14]=[CH:13][CH:12]=[C:11]2[Cl:23])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:24][C:25]1[C:29]([CH3:30])=[C:28]([NH2:31])[NH:27][N:26]=1.CCO>Cl.CC#N>[ClH:23].[C:1]([S:5]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH:20]([F:22])[F:21])[N:14]=[CH:13][CH:12]=[C:11]2[NH:31][C:28]1[NH:27][N:26]=[C:25]([CH3:24])[C:29]=1[CH3:30])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 702EthanolHCID 90047095HCID 90047095、化合物HCID 178434631HCID 178434631、化合物

生成物 1

HCID 178434683HCID 178434683、化合物収率 84.2%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To 6-(tert-butylsulfonyl)-4-chloro-7-(2,2-difluoroethoxy)quinoline (85 mg, 0.234 mmol) and 3,4-dimethyl-1H-pyrazol-5-amine (33.8 mg, 0.304 mmol) in a microwave vial was added EtOH (779 μl) followed by 1 drop of 1N aq HCl (8.52 mg, 0.234 mmol). The vial was sealed and heated to 80° C. behind a blast shield overnight. LCMS showed full conversion to product. Concentrated reaction and triturated resulting residue with ˜2 mL of MeCN using ˜1 min of sonication. Filtered resulting solid, rinsing with MeCN, and dried under vacuum resulting in the product 6-(tert-butylsulfonyl)-7-(2,2-difluoroethoxy)-N-(3,4-dimethyl-1H-pyrazol-5-yl)quinolin-4-amine, hydrochloride (93.5 mg, 0.197 mmol, 84% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.70 (s, 1H), 11.25 (br. s., 1H), 9.26 (br. s., 1H), 8.51 (d, J=7.07 Hz, 1H), 7.57 (s, 1H), 6.67 (d, J=7.33 Hz, 1H), 6.47 (tt, J=3.28, 53.81 Hz, 1H), 4.63 (td, J=3.16, 14.46 Hz, 2H), 2.24 (s, 3H), 1.84 (s, 3H), 1.34 (s, 9H). MS: m/z: 439.3 [M+H]+.

後処理

  1. customThe vial was sealed
  2. concentrationConcentrated
  3. customreaction
  4. customtriturated
  5. customresulting residue
  6. filtrationFiltered
  7. customresulting solid
  8. washrinsing with MeCN
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-1ccf77b2082141058e80bc5b264c1f7c
出典データセット
uspto-grants-2015_12
特許番号
US09216965B2

反応ノート

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