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

HRID 645491Notes

Reaction equation

HRID 645491 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-aef23442ebd141288d5b04ce6fa32f44
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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