Trifluoroacetic acid → HCID 11179038, compound

HRID 2375801Notes

Reaction equation

HRID 2375801 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:22][C:23]2[CH:27]=[C:26]([C:28]3[S:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[O:25][N:24]=2)[CH:7]=[C:8]([C:10](=[O:21])[NH:11][CH:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)[CH:9]=1)=[O:4].C(O)(C(F)(F)F)=O>C1COCC1.O>[Cl:33][C:30]1[S:29][C:28]([C:26]2[O:25][N:24]=[C:23]([CH2:22][N:6]3[CH:7]=[C:8]([C:10](=[O:21])[NH:11][CH:12]4[CH2:13][CH2:14][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH2:17]4)[CH:9]=[C:5]3[C:3]([OH:4])=[O:2])[CH:27]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11248874HCID 11248874, compound

Product 1

HCID 11179038HCID 11179038, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid methyl ester (example 16, 60 mg) in 15 mL of THF/water(3:1) was added LiOH monohydrate (50 mg) The mixture was stirred for 2 h at 45° C. whereupon it was cooled to RT, acidified with TFA and concentrated. 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-4-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid (33 mg) was obtained after HPLC purification (CH3CN/H2O gradient+0.05% TFA) of the crude product. MS (ESI+): m/e=477 [M+H]+, chloro pattern.

Workup

  1. temperaturewas cooled to RT
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-49ca9edeacf54865856078800a721f0b
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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