1,2-Dichloroethane → HCID 58504728, compound

HRID 2367425Notes

Reaction equation

HRID 2367425 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.[NH2:32][C:33]1[N:38]=[C:37]([C:39]2[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([F:47])[CH:40]=2)[CH:36]=[C:35]([N:48]2[CH2:53][C@@H:52]([NH2:54])[CH2:51][CH2:50][C@H:49]2[CH3:55])[N:34]=1>CN(C=O)C.O>[NH2:32][C:33]1[N:34]=[C:35]([N:48]2[C@H:49]([CH3:55])[CH2:50][CH2:51][C@H:52]([NH:54][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:53]2)[CH:36]=[C:37]([C:39]2[CH:46]=[CH:45][C:42]([C:43]#[N:44])=[C:41]([F:47])[CH:40]=2)[N:38]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 999Phenylacetic AcidHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 58504797HCID 58504797, compound

Product 1

HCID 58504728HCID 58504728, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A premixed solution of phenylacetic acid (45.0 mg, 0.331 mmol), EDC (79 mg, 0.413 mmol), HOBT (84 mg, 0.551 mmol), and N-methylmorpholine (0.152 mL, 1.378 mmol) in DMF (2 mL) was added to 4-{2-amino-6-[(2R,5S)-5-amino-2-methyl-1-piperidinyl]-4-pyrimidinyl}-2-fluorobenzonitrile (100 mg, 0.276 mmol) in DMF (2 mL). The solution was stirred at room temperature overnight. The reaction was diluted with water (10 mL), and then extracted with EtOAc (3×10 mL). The organics were combined, washed brine, dried over MgSO4, filtered and concentrated. The resulting oil was purified with a 10 g Biotage SNAP column with gradient of 0 to 85% EtOAc in Hexane for 25 minutes to afford the title compound (105 mg) as a yellow oil. LC-MS (ES) m/z=445 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified with a 10 g Biotage SNAP column with gradient of 0 to 85% EtOAc in Hexane for 25 minutes

Sources & evidence

ORD record
ord-9f1bed05097a421082e5df4b29ada670
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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