Phenylacetyl chloride → HCID 57383066, compound

HRID 2168256Notes

Reaction equation

HRID 2168256 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1[C:16]2[NH:17][CH:18]=[CH:19][C:15]=2[C:14]([N:20]2[CH2:25][CH2:24][CH:23]([NH2:26])[CH2:22][CH2:21]2)=[N:13][CH:12]=1.CN1CCOCC1>ClCCl.CN(C=O)C>[C:1]1([CH2:7][C:8]([NH:26][CH:23]2[CH2:22][CH2:21][N:20]([C:14]3[C:15]4[CH:19]=[CH:18][NH:17][C:16]=4[N:11]=[CH:12][N:13]=3)[CH2:25][CH2:24]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 79724-MethylmorpholineHCID 11564772HCID 11564772, compound

Product 1

HCID 57383066HCID 57383066, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Phenylacetyl chloride (0.037 g, 0.240 mmol, commercially available from e.g sigma-aldrich or fluka) in Dichloromethane (DCM) (1.5 ml) was added to a solution of 1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine D2 (0.043 g) and POL-NMM (0.279 g, 0.600 mmol) in DMF (1.5 ml). The mixture was shaked overnight at room temperature on a mini block. The resulting mixture was washed using DCM DMF (1:1) and the acid chloride left was removed using an NH2 cartridge. Then the solvents were evaporated overnight using the genevac. The crude was finally purified via MDAP using a formic acid method to obtain the desired product E51 in 24 mg. LCMS [M+H][email protected] min (2 min run)

Workup

  1. washThe resulting mixture was washed
  2. waitthe acid chloride left
  3. customwas removed
  4. customThen the solvents were evaporated overnight
  5. customThe crude was finally purified via MDAP

Sources & evidence

ORD record
ord-7312a5a517cb43b6b9a778ae9f017131
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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