HOAt → 2-Cyano-4-(cyclohexylmethylamino)pyrimidine-5-carboxylic acid(2-morpholin-4-yl-1-phenylethyl)amide

HRID 645491

反応式

HRID 645491 の反応式
[C:1]([C:3]1[N:8]=[C:7]([NH:9][CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:6]([C:17]([OH:19])=O)=[CH:5][N:4]=1)#[N:2].[N:20]1([CH2:26][CH:27]([NH2:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.CCN=C=NCCCN(C)C.Cl.O.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O>[N:20]1([CH2:26][CH:27]([NH:34][C:17]([C:6]2[C:7]([NH:9][CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[N:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[O:19])[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

参加物

7

反応物 4

HCID 181649HOAtHCID 28144622-(Morpholin-4-yl)-1-phenylethan-1-amineHCID 687033802-Cyano-4-(cyclohexylmethylamino)-pyrimidine-5-carboxylic acidHCID 87672115EDCl H2O

生成物 1

HCID 575803772-Cyano-4-(cyclohexylmethylamino)pyrimidine-5-carboxylic acid(2-morpholin-4-yl-1-phenylethyl)amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-cyano-4-(cyclohexylmethylamino)-pyrimidine-5-carboxylic acid (0.33 mmol, step 1.4) in DMF (2.0 mL) are added 2-morpholin-4-yl-1-phenylethylamine (69 mg, step 1.3), EDCl—H2O (0.50 mmol) and HOAt (0.50 mmol) at room temperature. After stirring at room temperature for 24 h, the reaction mixture is diluted with AcOEt. The mixture is washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by RP-HPLC to give the title compound; 1H NMR (DMSO) δ 0.6-1.08 (m, 2H), 1.20-1.35 (m, 3H), 1.65-1.78 (m, 6H), 2.48-2.53 (m, 2H), 2.60-2.62 (m, 2H), 2.87-2.93 (m, 2H), 3.31-3.35 (m, 1H), 3.36-3.44 (M, 1H), 3.60-3.68 (m, 4H), 5.29-5.35 (m, 1H), 7.34-7.36 (m, 1H), 7.43-7.47 (m, 2H), 7.50-7.52 (m, 2H), 8.86 (s, 1H), 9.00-9.04 (m, 1H), 9.21 (d, 1H).

後処理

  1. washThe mixture is washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue is purified by RP-HPLC

出典と根拠

ORDレコード
ord-aef23442ebd141288d5b04ce6fa32f44
出典データセット
uspto-grants-2010_04
特許番号
US07704996B2

関連ノート

読み込み中…