Ethylenediamine → HCID 58438604, compound

HRID 1898655Notes

Reaction equation

HRID 1898655 reaction equation
[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:43])[C@H:8]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([N:24]4[CH2:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][C:30]=5[Cl:33])[C:25]4=[O:34])[N:22]=3)[N:17](COCC[Si](C)(C)C)[CH:16]=2)=[O:14])[CH:9]2[CH2:11][CH2:10]2)[CH2:4]1)#[N:2].FC(F)(F)C(O)=O.C(N)CN>ClCCl>[C:1]([CH:3]1[CH2:6][N:5]([C:7](=[O:43])[C@H:8]([NH:12][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[C:21]([N:24]4[CH2:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][C:30]=5[Cl:33])[C:25]4=[O:34])[N:22]=3)[NH:17][CH:16]=2)=[O:14])[CH:9]2[CH2:10][CH2:11]2)[CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 67386178HCID 67386178, compound

Product 1

HCID 58438604HCID 58438604, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide (40 mg, 0.065 mmol) in dichloromethane (1 mL) at r.t. was added trifluoroacetic acid (0.30 mL, 3.87 mmol). The solution was stirred for 3 h at room temperature then concentrated under vacuum. The residue was dissolved in dichloromethane (1 mL) and ethylenediamine (0.43 mL, 6.45 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated under vacuum. The crude residue was suspended in water:EtOAc (2 mL: 5 mL) and the resultant solid was collected by filtration, washing with EtOAc, to afford 23 mg (73%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide as a white solid. MS: (M+Na)+=512.

Workup

  1. concentrationthen concentrated under vacuum
  2. dissolutionThe residue was dissolved in dichloromethane (1 mL)
  3. stirringThe reaction mixture was stirred at room temperature for 2 h
  4. concentrationthen concentrated under vacuum
  5. filtrationEtOAc (2 mL: 5 mL) and the resultant solid was collected by filtration
  6. washwashing with EtOAc

Sources & evidence

ORD record
ord-79943e04cf914fb0a6998ab785bb0c8d
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…