Triethylamine → N-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-methane sulfonamide

HRID 32363

反応式

HRID 32363 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][S:25]([CH3:24])(=[O:27])=[O:26])[S:3][C:4]=1[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[N:9]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4479614-(2-Amino-4-methyl-5-thiazolyl)-N-(3-nitrophenyl)-2-pyrimidinamine

生成物 1

HCID 10111991N-{4-Methyl-5-[2-(3-nitro-phenylamino)-pyrimidin-4-yl]-thiazol-2-yl}-methane sulfonamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(3-nitro-phenyl)-amine (1.0 mmol, 0.33 g) and methylsulfonyl chloride (2.0 mmol, 0.22 g) in dry DMF (2 mL) was added Et3N (0.28 mL). The reaction mixture was stirred at room temperature for 20 h. After cooling, the mixture was diluted with EtOAc, washed with brine, and dried over MgSO4. The solvent was evaporated and the residue was purified by preparative RP-HPLC using a gradient from 10-70% MeCN in 0.1% aq CF3COOH over 40 min. The title compound was obtained as an orange solid. Anal. RP-HPLC: tR=17.4 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >97%). 1H-NMR (DMSO-d6) δ: 3.10 (s, 3H, CH3), 3.25 (s, 3H, CH3), 7.05 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.42 (m, 1H, Ph-H), 7.63 (m, 1H, Ph-H), 7.98 (m, 1H, Ph-H), 8.21 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 8.42 (s, 1H, Ph-H), 9.18 (s, 1H, NH).

後処理

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated
  5. customthe residue was purified by preparative RP-HPLC
  6. customover 40 min

出典と根拠

ORDレコード
ord-b986295c70de44a182252c5ce92fbe6d
出典データセット
uspto-grants-2008_09
特許番号
US07427627B2

関連ノート

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