Trifluoroacetic acid → HCID 54755744, compound

HRID 2191572Notes

Reaction equation

HRID 2191572 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH:23]4[CH2:25][CH2:24]4)[N:21]=3)[N:16](COCC[Si](C)(C)C)[CH:15]=2)=[O:13])[CH2:6]1)(=[O:4])=[O:3].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([NH:11][C:12]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([CH:23]4[CH2:25][CH2:24]4)[N:21]=3)[NH:16][CH:15]=2)=[O:13])[CH2:6]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67002189HCID 67002189, compound

Product 1

HCID 54755744HCID 54755744, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10 mL round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-piperidin-3-yl)-amide (173 mg, 0.35 mmol) was dissolved in CH2Cl2 (1.4 mL). Trifluoroacetic acid (1.1 mL) was added and the light yellow reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was taken up in toluene (3 mL), concentrated and then dried under high vacuum. The residue was dissolved in CH2Cl2 (1.4 mL) and ethylenediamine (1.4 mL) was added. The reaction mixture was stirred at room temperature for 2 h then H2O and EtOAc were added. The resultant suspension was filtered, rinsing with H2O and EtOAc and dried under high vacuum to afford 103 mg (81%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-methanesulfonyl-piperidin-3-yl)-amide as an off-white solid. MS: (M+H)+=364; mp=284.0-287.0.

Workup

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried under high vacuum
  4. dissolutionThe residue was dissolved in CH2Cl2 (1.4 mL)
  5. additionethylenediamine (1.4 mL) was added
  6. stirringThe reaction mixture was stirred at room temperature for 2 h
  7. additionH2O and EtOAc were added
  8. filtrationThe resultant suspension was filtered
  9. washrinsing with H2O and EtOAc
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-d5ce5e260a8747dbaa4a8e6df6e84bce
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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