Carbon Tetrachloride → HCID 178433939、化合物

HRID 539077ノート

反応式

HRID 539077 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]([NH:29][NH:30][C:31](=[NH:33])[CH3:32])=O)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOC(C)=O.C(Cl)Cl.C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:12][O:11][C:10](=[O:13])[N:9]2[C:14]2[CH:19]=[CH:18][N:17]3[N:20]=[CH:21][C:22]([C:23]4[CH:35]=[CH:34][C:26]([C:27]5[NH:33][C:31]([CH3:32])=[N:30][N:29]=5)=[CH:25][CH:24]=4)=[C:16]3[N:15]=2)=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178465658HCID 178465658、化合物

生成物 1

HCID 178433939HCID 178433939、化合物収率 6.3%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 21877088Acetonitrile methylene chloride溶媒

反応条件

温度
50 °C

実験手順

A suspension of (S)-4-(5-(4-(4-fluorophenyl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)-N′-(1-iminoethyl)benzohydrazide (0.049 g, 0.104 mmol) in 1:1 DCM-acetonitrile (10 mL) was treated with carbon tetrachloride (0.040 mL, 0.414 mmol), triethylamine (0.1442 mL, 1.035 mmol) and triphenylphosphine (0.1086 g, 0.414 mmol) at ambient temperature. The mixture was heated at 50° C. for 2 hours. After cooing to ambient temperature, the mixture was treated with EtOAc, washed with water, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (2-5% MeOH in DCM) to provide (S)-4-(4-fluorophenyl)-3-(3-(4-(5-methyl-4H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.003 g, 6% yield) as a yellow oil. LCMS (APCI+) m/z 456 [M+H]+.

後処理

  1. customAfter cooing to ambient temperature
  2. washwashed with water
  3. customdried
  4. addition(phase separator silicone treated filter paper)
  5. concentrationconcentrated
  6. custompurified on silica gel (2-5% MeOH in DCM)

出典と根拠

ORDレコード
ord-216ee27aa9d741b689b0a5cdbb59023e
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

読み込み中…