Ethylenediamine → HCID 54755979, compound

HRID 2191579Notes

Reaction equation

HRID 2191579 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([NH:15][CH:16]4[C:21]([CH3:23])([CH3:22])[CH2:20][CH2:19][N:18]([S:24]([CH3:27])(=[O:26])=[O:25])[CH2:17]4)=[O:14])=[CH:11][N:10](COCC[Si](C)(C)C)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.C(N)CN>C(Cl)Cl>[CH3:27][S:24]([N:18]1[CH2:19][CH2:20][C:21]([CH3:23])([CH3:22])[CH:16]([NH:15][C:13]([C:12]2[C:6]3[C:7](=[N:8][CH:9]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[N:5]=3)[NH:10][CH:11]=2)=[O:14])[CH2:17]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 670023555H-Pyrrolo[2,3-b]pyrazine-7-carboxamide, 2-cyclopropyl-N-[4,4-dimethyl-1-(methylsulfonyl)-3-piperidinyl]-5-[[2-(trimethylsilyl)ethoxy]methyl]-

Product 1

HCID 54755979HCID 54755979, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-cyclopropyl-N-(4,4-dimethyl-1-(methylsulfonyl)piperidin-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (143 mg, 0.27 mmol) in CH2Cl2 (5 mL) was added TFA (2.0 mL, 26.0 mmol). The yellow reaction mixture was stirred for 3 h then concentrated The residue was redissolved in CH2Cl2 (5 mL) and ethylenediamine (0.5 mL, 7.4 mmol) was added. The reaction mixture was stirred at for 1 h then concentrated. The residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes to 5% MeOH/EtOAc) to isolate 66 mg (62%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-4,4-dimethyl-piperidin-3-yl)-amide as a white solid. MS: (M+H)+=392.

Workup

  1. concentrationthen concentrated The residue
  2. dissolutionwas redissolved in CH2Cl2 (5 mL)
  3. stirringThe reaction mixture was stirred at for 1 h
  4. concentrationthen concentrated
  5. customThe residue was purified by SiO2 chromatography (50% to 100% EtOAc/hexanes to 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-c49bfb8f63b34fcbbe0b6895d54f2d4c
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

Loading…