Trifluoroacetic acid → HCID 86757030, compound

HRID 1068215Notes

Reaction equation

[N:1]1[C:2]([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)=[CH:3][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[C:2]([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[CH2:44][CH2:45][CH2:46]4)([CH3:42])[C:30]([OH:32])=[O:31])[CH2:18]3)[CH2:12][CH2:11]2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 86757031HCID 86757031, compound

Product 1

HCID 86757030HCID 86757030, compoundYield 104.3%

Procedure

The title compound was prepared from 19 mg of α-(R)-(3-(S)-((4-(imidazo[1,2-a]pyridin-2-yl)-piperidine-1-yl)methyl)-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-cyclobutylpropanoic acid, 4-methoxy-benzyl ester (from Step C), 2 mL of TFA and 0.2 mL of anisole, using a procedure analogous to that described in Example 235, Step D to provide 16 mg of the title compound as a foamy solid. 1H NMR (500 MHz, CD3OD): δ1.45-1.64 (m, 6H), 1.83-2.04 (m, 6H), 2.30(t, J=14.2 Hz, 3H), 2.68-3.85(m, 12H), 6.93 (t, J=6.3 Hz, 1H), 7.27 (d, J=6.7 Hz, 2H), 7.35 (t, J=6.7 Hz, 1H), 7.45 (dd, J=13.6, 6.3Hz, 1H), 7.49 (d, J=13.5 Hz, 1H), 7.67 (s, 1H), 8.38 (d, J=6.9 Hz, 1H). ESI-MS 505 (M+H); HPLC A 2.21 min.

Sources & evidence

ORD record: ord-e30058f44d5f49e98ec8cb3adf146095
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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