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

HRID 645491노트

반응식

HRID 645491 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aef23442ebd141288d5b04ce6fa32f44
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704996B2

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