1,2-Dichloroethane → HCID 58504417, compound

HRID 2367467Notes

Reaction equation

HRID 2367467 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](O)=[O:15])[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.[Cl:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44]>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:44][C:43]3[CH:45]=[CH:46][CH:47]=[C:41]([Cl:40])[CH:42]=3)=[O:15])[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 79323-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 58504706(3S)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-3-piperidinecarboxylic acid

Product 1

HCID 58504417HCID 58504417, compoundYield 97.5%

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 (150 mg, 0.439 mmol), EDC (118 mg, 0.615 mmol), and HOBT (83 mg, 0.615 mmol) in DMF (3 mL) was added 3-chloroaniline (56 mg, 0.44 mmol), and the 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 (193 mg) as a yellow solid. LC-MS (ES) m/z=451 [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-656f84d588494922b48f7853076b05e6
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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