Trifluoroacetic acid → HCID 178474033, compound

HRID 537070Notes

Reaction equation

HRID 537070 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[C:14]1[O:18][C:17]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([NH:26][C:27](=[O:29])[CH3:28])[CH:20]=2)=[CH:16][C:15]=1[C:30]1[N:34]=[CH:33][N:32](COCC[Si](C)(C)C)[N:31]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:4][C:3]=1[C:14]1[O:18][C:17]([C:19]2[C:24]([CH3:25])=[CH:23][N:22]=[C:21]([NH:26][C:27](=[O:29])[CH3:28])[CH:20]=2)=[CH:16][C:15]=1[C:30]1[NH:34][CH:33]=[N:32][N:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66749388N-(4-{5-[2-chloro-5-(pyrrolidin-1-ylmethyl)phenyl]-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-furyl}-5-methylpyridin-2-yl)acetamide

Product 1

HCID 178474033HCID 178474033, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-{5-[2-chloro-5-(pyrrolidin-1-ylmethyl)phenyl]-4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-2-furyl}-5-methylpyridin-2-yl)acetamide (0.20 g, 0.34 mmol) in DCM (5 mL) was added TFA (2 mL). The mixture was allowed to stir at rt overnight. The mixture was concentrated and the residue was purified by column chromatography to give N-(4-{5-[2-chloro-5-(pyrrolidin-1-ylmethyl)phenyl]-4-(4H-1,2,4-triazol-3-yl)-2-furyl}-5-methylpyridin-2-yl)acetamide (0.14 g, 81%). LCMS (FA): m/z=477.6 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4fd36a0f84424a78a9c6a8e6425807b2
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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