Ammonia → HCID 46908651, compound

HRID 1159684Notes

Reaction equation

HRID 1159684 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9](O)=[O:10])=[C:6]([N:12]([CH3:14])[CH3:13])[N:5]=[C:4]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[O:24])=[CH:18][CH:17]=2)[N:3]=1.C(N1C=CN=C1)([N:37]1C=CN=C1)=O.N>C1COCC1>[NH2:37][C:9](=[O:10])[CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=3)=[O:24])=[CH:18][CH:17]=2)=[N:5][C:6]=1[N:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 9826188HCID 9826188, compound

Product 1

HCID 46908651HCID 46908651, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4-chloro-6-(dimethylamino)-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetic acid (0.940 g, 1.98 mmol) in THF (18 mL) was added 1,1′-carbonyldiimidazole (0.353 mg, 2.18 mmol). The reaction mixture was stirred at room temperature for 2 hours followed by the addition of aqueous ammonia solution (28% NH3, 0.94 mL). After stirring for 16 hours at room temperature, the reaction mixture was partitioned between EtOAc and water and the separated organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo and the remaining residue was passed through a short pad of silica gel. Removal of acidic impurities via PS-carbonate resin then gave N-(4-{[5-(2-amino-2-oxoethyl)-4-chloro-6-(dimethylamino)pyrimidin-2-yl]methyl}phenyl)-2-naphthamide as a white solid (0.670 g, 71%).

Workup

  1. stirringAfter stirring for 16 hours at room temperature
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washthe separated organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customRemoval of acidic impurities via PS-carbonate resin

Sources & evidence

ORD record
ord-b6157799c3354af387ffb1e22aa51a35
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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