HOAt → (r)-2-Cyano-4-(spiro[2.5]oct-6-ylmethyl)pyrimidine-5-carboxylic acid (2-phenyl 1-pyrrolidin-1-ylmethylethyl)amide

HRID 645508

Reaction equation

HRID 645508 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][CH:10]2[CH2:17][CH2:16][C:13]3([CH2:15][CH2:14]3)[CH2:12][CH2:11]2)[C:6]([C:18]([OH:20])=O)=[CH:5][N:4]=1)#[N:2].[C:21]1([CH2:27][C@@H:28]([NH2:35])[CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.O.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[C:21]1([CH2:27][C@@H:28]([NH:35][C:18]([C:6]2[C:7]([CH2:9][CH:10]3[CH2:11][CH2:12][C:13]4([CH2:14][CH2:15]4)[CH2:16][CH2:17]3)=[N:8][C:3]([C:1]#[N:2])=[N:4][CH:5]=2)=[O:20])[CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 181649HOAtHCID 12184138(r)-2-Phenyl-1-pyrrolidin-1-ylmethylethylamineHCID 687032762-Cyano-4-(spiro[2.5]oct-6-ylmethyl)pyrimidine-5-carboxylic acidHCID 87672115EDCl H2O

Product 1

HCID 91139520(r)-2-Cyano-4-(spiro[2.5]oct-6-ylmethyl)pyrimidine-5-carboxylic acid (2-phenyl 1-pyrrolidin-1-ylmethylethyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude 2-cyano-4-(spiro[2.5]oct-6-ylmethyl)pyrimidine-5-carboxylic acid (22 mg, step 74.5) in DMF (1.5 mL) are added (R)-2-phenyl-1-pyrrolidin-1-ylmethylethylamine (0.083 mmol), EDCl—H2O (0.11 mmol), and HOAt (0.11 mmol) at room temperature. The reaction mixture is stirred for 24 h and the reaction is quenched by the addition of H2O. The mixture is extracted with AcOEt, and the organic extracts are dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by RP-HPLC to give the title compound; MS (M+1)+: 474, Rf (solvent): 0.63 (CH2Cl2:MeOH=10:1).

Workup

  1. customthe reaction is quenched by the addition of H2O
  2. extractionThe mixture is extracted with AcOEt
  3. dry with materialthe organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-ebbaec1b7fa74d20b57f0e984fa021c0
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Linked notes

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