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Triethylamine → HCID 86595018、化合物

HRID 2216311
ノート
印刷プレビュー

反応式

HRID 2216311 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.C(N(CC)CC)C.[F:35][C:36]([F:42])([F:41])[S:37](Cl)(=[O:39])=[O:38].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][S:37]([C:36]([F:42])([F:41])[F:35])(=[O:39])=[O:38])=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 11361091HCID 11361091、化合物

生成物 1

HCID 86595018HCID 86595018、化合物収率 91.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of 4-[2-methyl-4-(2,4,6-trimethyl-phenylamino)-pyrimidine-5-sulfonyl]-phenol (122 mg, 0.318 mmol), prepared by the method described in Example 2, and triethylamine (0.053 mL, 0.38 mmol) in CH2Cl2 (3 mL) was added trifluoromethanesulfonyl chloride (0.037 mL, 0.35 mmol) at 0° C. The reaction mixture was stirred under N2 and slowly warmed to room temperature. The mixture was treated with saturated aqueous NaHCO3, and extracted (3×) with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc) to provide trifluoromethanesulfonic acid 4-[2-methyl-4-(2,4,6-trimethylphenylamino)-pyrimidine-5-sulfonyl]-phenyl ester (150 mg, 91%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.79 (s, 1H), 8.15 (br s, 1H), 8.08 (d, J=8.9 Hz, 2H), 7.47 (d, J=8.9 Hz, 2H), 6.92 (s, 2H), 2.42 (s, 3H), 2.31 (s, 3H), 1.98 (s, 6H); ESI MS m/z 516 [(M+H)+, calcd for C21H21F3N3O5S2, 516.1].

後処理

  1. extractionextracted (3×) with CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (67:33 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-2b7b9432488b4c75bf570460215c6864
出典データセット
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07112585B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート