1,2-Dichloroethane → (3S)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(2-methylphenyl)-3-piperidinecarboxamide

HRID 2367459Notes

Reaction equation

HRID 2367459 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=O)[CH2:9]2)[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)[N:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:40][C:41]1[C:42]([CH3:47])=[CH:43][CH:44]=[CH:45][CH:46]=1>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([NH:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[CH3:47])=[O:16])[CH2:9]2)[CH:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)[N:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7242O-ToluidineHCID 757711-HydroxybenzotriazoleHCID 58504706(3S)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-3-piperidinecarboxylic acid

Product 1

HCID 58504438(3S)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-(2-methylphenyl)-3-piperidinecarboxamideYield 49.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3S)-1-[2-amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-3-piperidinecarboxylic acid (146 mg, 0.428 mmol), EDC (115, 0.599 mmol), and HOBT (81 mg, 0.599 mmol) in DMF (8 mL) was added o-toluidine (64 mg, 0.60 mmol), and the reaction mixture was stirred at room temperature for 4 hours. LCMS showed reaction was completed. The reaction was poured onto water, and EtOAc was added to extract the product. The product stayed in the EtOAc layer. The organic solution was concentrated to dryness to give the title compound (92 mg) as a yellow solid. LC-MS (ES) m/z=431 [M+H]+.

Workup

  1. customreaction
  2. additionwas added
  3. extractionto extract the product
  4. concentrationThe organic solution was concentrated to dryness

Sources & evidence

ORD record
ord-94f8e9a854634a3da7ab5f216b7e067f
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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