Trifluoroacetic acid → HCID 59275351, compound

HRID 1025151Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[C:25]([C:27](=[O:33])[NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH:24]=[CH:23][C:22]=4[O:34][CH2:35]C4CCCNC4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[C:42](O)([C:44](F)(F)F)=O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[C:25]([C:27](=[O:33])[NH:28][CH2:29][CH:30]([CH3:31])[CH3:32])[CH:24]=[CH:23][C:22]=4[O:34][CH2:35][C:44]4[CH:42]=[CH:16][N:15]=[CH:13][CH:12]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59275571HCID 59275571, compound

Product 1

HCID 59275351HCID 59275351, compound

Procedure

2-(4-Fluorophenyl)-5-(5-(isobutylcarbamoyl)-2-(piperidin-3-ylmethoxy)phenyl)-N-methyl benzofuran-3-carboxamide, TFA. 1H NMR (400 MHz, THF-d8) δ ppm 0.93 (d, J=6.78 Hz, 6 H), 1.40-1.57 (m, 1 H), 1.75-2.00 (m, 4 H), 2.33 (br. s., 1 H), 2.80-3.00 (m, 5 H), 3.18 (t, J=6.40 Hz, 2 H), 3.32 (d, J=12.05 Hz, 1 H), 3.45 (d, J=10.79 Hz, 1 H), 3.90-4.12 (m, 2 H), 7.03 (d, J=8.53 Hz, 1 H), 7.22 (t, J=8.78 Hz, 2 H), 7.47 (dd, J=8.53, 1.51 Hz, 1 H), 7.58 (d, J=8.53 Hz, 1 H), 7.71 (t, J=5.65 Hz, 1 H), 7.75-7.86 (m, 2 H), 7.92 (s, 2 H), 8.01 (dd, J=8.78, 5.52 Hz, 2 H). LCMS m/z 558.20 (M+H), Rt 1.595 min. HPLC Rt 6.443 min. (Sunfire C18), 99.2% purity and 10.418 min. (XBridge Phenyl C18), 99.2% purity.

Workup

customHPLC Rt 6.443 min. (Sunfire C18), 99.2% purity and 10.418 min. (XBridge Phenyl C18), 99.2% purity

Sources & evidence

ORD record: ord-78468410a8de4633ad290e746fc9c0cd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722688B2

Reaction notes

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