Hydrochloric Acid → 5-Methyl-pyridine-2-sulfonic acid [2-{2-[(3-ethyl-ureido)-methyl]-pyridin-4-yl}-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

HRID 1066515ノート

反応式

HRID 1066515 の反応式
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)(=[O:19])=[O:18])[C:13]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:12]([O:36][CH3:37])[N:11]=2)[CH:7]=[CH:6][N:5]=1.C(N(CC)CC)C.[CH2:45]([N:47]=[C:48]=[O:49])[CH3:46].Cl>C1(C)C=CC=CC=1.C(Cl)Cl.CO>[CH2:45]([NH:47][C:48](=[O:49])[NH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)(=[O:19])=[O:18])[C:13]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:12]([O:36][CH3:37])[N:11]=2)[CH:7]=[CH:6][N:5]=1)[CH3:46]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 867569945-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride2 回

生成物 1

HCID 572347755-Methyl-pyridine-2-sulfonic acid [2-{2-[(3-ethyl-ureido)-methyl]-pyridin-4-yl}-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

A solution of 70 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride, product of example 30 b), in toluene (5 ml), was treated at RT with 26 mg of triethyamine then with 10 mg of ethylisocyanate and refluxed for 1 h until the reaction was complete according to TLC analysis (CH2Cl2/MeOH: 95/5). The mixture was poured into cold diluted HCl and the product extracted into CH2Cl2. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The solid residue was crystallised from CH2Cl2/Et2O to afford 5-methyl-pyridine-2-sulfonic acid [2-{2-[(3-ethyl-ureido)-methyl]-pyridin-4-yl}-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as off-white crystals. ISP mass spectrum, m/e 580.1 (M+1 calculated for C27H29N7O6S: 580).

後処理

  1. extractionthe product extracted into CH2Cl2
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe solid residue was crystallised from CH2Cl2/Et2O

出典と根拠

ORDレコード
ord-79e8403d150845a8817234f4ad9f1886
出典データセット
uspto-grants-2001_06
特許番号
US06242601B1

反応ノート

読み込み中…