Trifluoroacetic acid → HCID 59275212, compound

HRID 1877631Notes

Reaction equation

HRID 1877631 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[NH:12][C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:15][CH2:14]2)=[CH:7][C:6]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:30][C:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)=[C:28]([C:38]([NH:40][CH3:41])=[O:39])[C:27]=2[CH:42]=1.C(O)(C(F)(F)F)=[O:44]>CO.O.O.CO.C(#N)C.O.C(#N)C>[NH2:1][C:2](=[O:44])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[NH:12][C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:14][CH2:15]2)=[CH:7][C:6]=1[C:23]1[CH:24]=[CH:25][C:26]2[O:30][C:29]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)=[C:28]([C:38]([NH:40][CH3:41])=[O:39])[C:27]=2[CH:42]=1

Participants

8

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59275585HCID 59275585, compound

Product 1

HCID 59275212HCID 59275212, compound

Reagents, catalysts & solvents 5

HCID 887MethanolSolvent2×HCID 962WaterSolvent6×HCID 6342AcetonitrileSolvent4×HCID 18373917Acetonitrile--water (1/1)SolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

5-(2-(2-Aminoethoxy)-5-(1-(pyridin-2-yl)cyclopropylcarbamoyl)phenyl)-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide, 2 TFA. The LC/MS data was obtained on a Shimadzu analytical LC/Micromass Platform LC (ESI+) at 220 nm using the following set of conditions: Phenomenex Luna 3 μm C18, 2×50 mm column, with a gradient of 0-100% B (B=90% HPLC grade acetonitrile/0.1% trifluoroacetic acid/10% HPLC grade water), (A=90% HPLC grade water/0.1% trifluoroacetic acid/10% HPLC grade acetonitrile), in 4 minutes with a 1 minute hold at a rate of 0.8 mL/minute. HPLC purity was determined using a Shimadzu analytical LC at 254 nm and 256 nm with a Waters Sunfire C18 3.5 μm 4.6×150 mm column employing water/acetonitrile/0.1% trifluoroacetic acid with a gradient of 10-100% B (B=95% HPLC grade acetonitrile/0.1% trifluoroacetic acid/5% HPLC grade water), (A=95% HPLC grade water/0.1% trifluoroacetic acid/5% HPLC grade acetonitrile), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. The HPLC purity was then confirmed with an orthogonal solvent system and column using a Shimadzu analytical LC with a Waters XBridge Phenyl C18 3.5 μm 4.6×150 mm column employing water/methanol/10 mM ammonium bicarbonate with a gradient of 10-100% B (B=95% HPLC grade methanol/10 mM ammonium bicarbonate/5% HPLC grade water), (A=95% HPLC grade water/10 mM ammonium bicarbonate/5% HPLC grade methanol), in 10 minutes with a 10 minute hold at a rate of 1 mL/minute. 1H NMR (400 MHz, THF-d8) δ ppm 1.23-1.33 (m, 2H), 1.60-1.67 (m, 2H), 2.89 (d, J=4.77 Hz, 3H), 3.41 (t, J=5.14 Hz, 2H), 4.40 (t, J=5.14 Hz, 2H), 6.58 (br. s., 2H), 7.01-7.11 (m, 1H), 7.16-7.29 (m, 3H), 7.46 (d, J=8.03 Hz, 1H), 7.52-7.70 (m, 4H), 7.93 (dd, J=8.53, 2.26 Hz, 1H), 7.98-8.05 (m, 3H), 8.07 (s, 1H), 8.41 (d, J=4.77 Hz, 1H), 8.56 (s, 1H). LCMS m/z 565.4 (M+H), Rt=1.628 min. HPLC (Sunfire C18) Rt=5.048 min., 99.9% purity and (XBridge Phenyl C18) Rt=10.531 min., 100% purity.

Workup

  1. customThe LC/MS data was obtained on a Shimadzu analytical LC/Micromass Platform LC (ESI+) at 220 nm

Sources & evidence

ORD record
ord-a8b303c3a020410a8aff0d853755d612
Source dataset
uspto-grants-2012_11
Patent number
US08309558B2

Reaction notes

Loading…