Trifluoroacetic acid → HCID 86757028, compound

HRID 1068212Notes

Reaction equation

HRID 1068212 reaction equation
[N:1]1[CH:2]=[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@@:29]([CH:43]4[CH2:46][CH2:45][CH2:44]4)([CH3:42])[C:30]([O:32]CC4C=CC(OC)=CC=4)=[O:31])[CH2:18]3)[CH2:12][CH2:11]2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[N:1]1[CH:2]=[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C@@H:17]3[C@@H:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=4)[CH2:20][N:19]([C@@:29]([CH:43]4[CH2:44][CH2:45][CH2:46]4)([CH3:42])[C:30]([OH:32])=[O:31])[CH2:18]3)[CH2:14][CH2:15]2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86757029HCID 86757029, compound

Product 1

HCID 86757028HCID 86757028, compoundYield 109.5%

Procedure

To 26 mg of α-(R)-(3-(S)-((4-(imidazo[1,2-a]pyridin-3-yl)-piperidine-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-cyclobutylpropanoic acid, 4-methoxy-benzyl ester (from Step C) was added 2 mL of TFA and 0.3 mL of anisole. The reaction was stirred at r.t. for 1 hour. The reaction mixture was concentrated and the residue was purified by flash chromatography with 10% MeOH in CH2Cl2, followed by 15% MeOH and 1% NH4OH in CHCl3 to provide 23 mg of a foamy solid. 1H NMR (500 MHz, CD3OD): δ1.63-1.81 (m, 4H), 1.93-2.15 (m, 5H), 2.33(t, J=15.6 Hz, 2H), 2.44(m, 1H), 2.86(m, 1H), 3.00(d, J=13.8 Hz, 1H), 3.15-3.89(m, 13H), 7.11 (m, 1H), 7.28 (m, 2H), 7.39-7.48 (m, 2H), 7.75 (s, 1H), 7.85 (m, 2H) 8.32 (d, J=6.9 Hz, 1H). ESI-MS 505 (M+H); BLC A 1.64 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-893132444035418c91c6a4a6d1a30200
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…