Triethylamine → HCID 59565293、化合物

HRID 1962885ノート

反応式

HRID 1962885 の反応式
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:18][CH3:19])[C:15]([OH:17])=O)=[C:8]([F:20])[C:7]=2[CH3:21])#[CH:2].CN(C(ON1N=[N:37][C:32]2[CH:33]=CC=C[C:31]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:44]CN(CC)CC.[NH4+].[Cl-]>CC#N.C(N)(C)(C)C>[C:32]([NH:37][C:15](=[O:17])[CH:14]([O:13][C:9]1[CH:10]=[C:11]2[C:6](=[C:7]([CH3:21])[C:8]=1[F:20])[N:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:12]2)[S:18][CH3:19])([CH3:44])([CH3:33])[CH3:31]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86647256HCID 86647256、化合物

生成物 1

HCID 59565293HCID 59565293、化合物

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6385Tert-Butylamine溶媒

実験手順

To a mixture containing (3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-methylsulfanyl-acetic acid (250 mg) from Step 8, aza-HOBT (116 mg), TBTU (273 mg) and Et3N (0.32 ml) in CH3CN (12 ml), tert-butyl amine was added at room temperature, under a nitrogen atmosphere. The resulting brown suspension was stirred 1 hour at room temperature then poured into aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulphate anhydrous, filtered and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate) to give N-tert-butyl-2-(3-ethynyl-7-fluoro-8-methyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (201 mg) as white solid. 1H NMR (CDCl3) δ ppm: 8.88 (1H, d); 8.17 1H, d); 7.17 (1H, d); 6.64 (1H, br s); 5.59 (1H, s); 3.27 (1H, s); 2.69 (3H, d); 2.18 (3H, s); 1.44 (9H, s).

後処理

  1. additionwas added at room temperature, under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-6f4b6c90448d43878ad4cb0bda834a24
出典データセット
uspto-grants-2013_04
特許番号
US08415272B2

反応ノート

読み込み中…