Potassium Carbonate → HCID 117777429、化合物

HRID 64180

反応式

HRID 64180 の反応式
Br[C:2]1[CH:31]=[CH:30][C:5]2[N:6]([C:9]3[CH:10]=[C:11]([NH:23][S:24]([CH:27]4[CH2:29][CH2:28]4)(=[O:26])=[O:25])[CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=4[F:22])[CH:14]=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[CH3:39].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I>[CH2:38]([N:40]1[CH2:45][CH2:44][N:43]([C:2]2[CH:31]=[CH:30][C:5]3[N:6]([C:9]4[CH:10]=[C:11]([NH:23][S:24]([CH:27]5[CH2:29][CH2:28]5)(=[O:26])=[O:25])[CH:12]=[C:13]([C:15]5[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=5[F:22])[CH:14]=4)[CH:7]=[N:8][C:4]=3[CH:3]=2)[CH2:42][CH2:41]1)[CH3:39]

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 791961-EthylpiperazineHCID 145742L-ProlineHCID 89501045N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

生成物 1

HCID 117777429HCID 117777429、化合物収率 18%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of the compound of N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (110 mg, 0.198 mmol) in DMSO was added potassium carbonate (54 mg, 0.391 mmol, 2.0 eq.). The mixture was degassed by N2 bubbling for 10 min followed by addition of 1-ethylpiperazine (68 mg, 0.595 mmol, 3.0 eq.) and L-proline (4.5 mg) and CuI (3 mg). Then seal tube was closed and the mixture was kept at 95° C. for 24 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to give the product in 18% yield (20 mg). 1H NMR (400 MHz, DMSO-D6): δ10.3 (s, 1H), 8.98 (s, 1H), 7.77 (m, 1H), 7.66 (s, 1H), 7.60 (brs, 2H), 7.50 (brs, 2H), 7.41 (s, 1H), 7.33-7.27 (m, 2H), 3.60 (m, 4H), 3.29-3.20 (m, 4H), 3.02 (q, 2H), 2.90 (t, 1H), 1.30 (t, 3H), 1.04 (q, 4H), LC-MS (ESI): Calculated mass: 537.62; Observed mass: 538.1 [M+H]+

後処理

  1. customThe mixture was degassed by N2 bubbling for 10 min
  2. customThen seal tube
  3. customwas closed
  4. customThe mixture was quenched
  5. extractionextracted as in Example 1(d)
  6. distillationThe solvent was distilled off

出典と根拠

ORDレコード
ord-5c2d842e7c0f4712a8e85d08303f3378
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

関連ノート

読み込み中…