1,2-Dichloroethane → HCID 58504535, compound

HRID 2367473Notes

Reaction equation

HRID 2367473 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.[CH3:40][CH:41]1[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]1>CN(C=O)C.CCOC(C)=O.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:47][CH:44]3[CH2:45][CH2:46][CH:41]([CH3:40])[CH2:42][CH2:43]3)=[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

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 806044-MethylcyclohexylamineHCID 58504706(3S)-1-[2-Amino-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-3-piperidinecarboxylic acid

Product 1

HCID 58504535HCID 58504535, compoundYield 99.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 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) into a 100 mL round-bottomed flask was added 4-methylcyclohexanamine (50 mg, 0.44 mmol), and The mixture was stirred at room temperature for 4 hours. LCMS showed the reaction was completed. The reaction was poured into 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 (190 mg) as a yellow solid. LC-MS (ES) m/z=437 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-ea69ebcbc0864bcd8e03dced7ddae618
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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