Triethylamine → 3-(6-Bromo-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2265935ノート

反応式

HRID 2265935 の反応式
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=1.C(N(CC)CC)C.[Br:25][C:26]1[N:31]=[CH:30][C:29]([CH:32]=[CH:33][C:34](O)=[O:35])=[CH:28][CH:27]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C1COCC1.CCOC(C)=O>[Br:25][C:26]1[N:31]=[CH:30][C:29]([CH:32]=[CH:33][C:34]([NH:2][CH2:3][C:4]2[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=2)=[O:35])=[CH:28][CH:27]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 534149813-(6-Bromopyridin-3-yl)prop-2-enoic acidHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

生成物 1

HCID 723356663-(6-Bromo-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide収率 72%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (63 mg, 0.219 mmol) was suspended in THF and treated with triethylamine (25 mg, 0.241 mmol) and then the resulting mixture was stirred for 10 mins. 3-(6-bromo-pyridin-3-yl)-acrylic acid (50 mg, 0.219 mmol) was added to the reaction mixture followed by DMTMM (66 mg, 0.241 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat'd NaHCO3 (×2), and brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was recrystallized (EtOAc/n-Hexane) to yield the title compound (71 mg, 72%).

後処理

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. washThe resulting solution was washed successively with water, sat'd NaHCO3 (×2), and brine
  3. customdried over anhyd
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was recrystallized (EtOAc/n-Hexane)

出典と根拠

ORDレコード
ord-3f21e27a6df04eaaa6a59f920f73543f
出典データセット
uspto-grants-2010_12
特許番号
US07858621B2

反応ノート

読み込み中…