Ethyl Acetate → N-(3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide

HRID 1050154Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C:27](O)=[O:28])=[C:22]([F:30])[CH:21]=2)[CH:7]=[N:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH3:2].[NH:31]1[CH:35]=[C:34]([C:36]2[CH:37]=[C:38]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=2)[NH2:39])[CH:33]=[N:32]1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.CC(=O)OCC>N1C=CC=CC=1.O>[NH:31]1[CH:35]=[C:34]([C:36]2[CH:37]=[C:38]([NH:39][C:27](=[O:28])[CH2:26][C:23]3[CH:24]=[CH:25][C:20]([C:6]4[CH:7]=[N:8][C:9]([O:10][CH2:11][C:12]5[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=5)=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=4)=[CH:21][C:22]=3[F:30])[CH:40]=[C:41]([C:43]([F:45])([F:46])[F:44])[CH:42]=2)[CH:33]=[N:32]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a mixture of 2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetic acid (15 mg, 0.036 mmol) in pyridine (3 mL) were added 3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)aniline (8.28 mg, 0.036 mmol) and T3P® (EA solvate) (0.5 mL, 0.036 mmol). The mixture was stirred at 25° C. for 1 h. The mixture was added to water and concentrated to afford N-(3-(1H-pyrazol-4-yl)-5-(trifluoromethyl)phenyl)-2-(4-(5-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)acetamide (50 mg, 0.024 mmol, 66.3% yield). TLC (DCM/MeOH=15:1, Rf=0.5): 1H NMR (400 MHz, CD3OD) δ 8.02 (s, 1H), 7.82 (s, 1H), 7.58 (s, 1H), 7.37 (s, 2H), 7.32-7.30 (m, 4H), 7.25-7.23 (m, 2H), 6.89-6.86 (m, 3H), 5.36 (s, 2H), 4.15-4.09 (m, 2H), 3.83 (s, 2H), 3.77 (s, 3H), 1.46 (t, J=6.8 Hz, 3H). ES-LCMS m/z 621.2 (M+H).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-a846820150f04e3fac5c5860768754ae
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382238B2

Reaction notes

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