Trifluoroacetic acid → HCID 58438561, compound

HRID 1898613Notes

Reaction equation

HRID 1898613 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:44])[C@H:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]4[N:27]=[N:28][N:29]([CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH:30]=4)[N:24]=3)[N:19](COCC[Si](C)(C)C)[CH:18]=2)=[O:16])[CH:11]2[CH2:13][CH2:12]2)[CH2:5][CH2:4]1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:44])[C@H:10]([NH:14][C:15]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[C:23]([C:26]4[N:27]=[N:28][N:29]([CH:31]5[CH2:35][CH2:34][CH2:33][CH2:32]5)[CH:30]=4)[N:24]=3)[NH:19][CH:18]=2)=[O:16])[CH:11]2[CH2:12][CH2:13]2)[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67386358HCID 67386358, compound

Product 1

HCID 58438561HCID 58438561, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1-cyclopentyl-1H-[1,2,3]triazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide (85 mg, 0.14 mmol) in CH2Cl2 (4 mL) was added TFA (2.0 mL). The reaction mixture was stirred at room temp for 3 h then concentrated. The residue was redissolved in CH2Cl2 (4 mL) and ethylenediamine (0.5 mL) was added. The reaction mixture was stirred at room temp for 0.5 h then concentrated. The residue was purified twice by silica gel chromatography (50% to 100% EtOAc/hexanes to 5% MeOH/EtOAc then 0% to 5% MeOH/CH2Cl2 (0.5% NH4OH)) then triturated with Et2O to isolate 35 mg (52%) of 2-(1-cyclopentyl-1H-[1,2,3]triazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-cyclopropyl-2-oxo-ethyl]-amide as a white powder. MS: (M+H)+=488.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe residue was redissolved in CH2Cl2 (4 mL)
  3. additionethylenediamine (0.5 mL) was added
  4. stirringThe reaction mixture was stirred at room temp for 0.5 h
  5. concentrationthen concentrated
  6. customThe residue was purified twice by silica gel chromatography (50% to 100% EtOAc/hexanes to 5% MeOH/EtOAc
  7. custom0% to 5% MeOH/CH2Cl2 (0.5% NH4OH)) then triturated with Et2O

Sources & evidence

ORD record
ord-ff09460309624fd7b9d914d8b77f7329
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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