Triethylamine → HCID 86728489, compound

HRID 1053184Notes

Reaction equation

HRID 1053184 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:14][C:15]2[CH:16]=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:49][O:50][C:51]1[CH:56]=[C:55]([NH2:57])[CH:54]=[CH:53][N:52]=1.C(N(CC)CC)C>ClCCl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:57][C:55]2[CH:54]=[CH:53][N:52]=[C:51]([O:50][CH3:49])[CH:56]=2)=[O:11])=[C:7]([O:14][C:15]2[CH:16]=[N:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2808912-Methoxypyridin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68760286HCID 68760286, compound

Product 1

HCID 86728489HCID 86728489, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(tert-butyl)-2((6-(trifluoromethyl)pyridin-3-yl)oxy)benzoic acid (169.7 mg, 0.5 mmol), HATU (190 mg, 0.5 mmol), 2-methoxypyridin-4-amine (62.1 mg, 0.5 mmol) and tri-ethyl amine (278.8 μL, 2 mmol) in dichloromethane (5 mL) was stirred at room temperature over 72 hours. The reaction was purified by silica gel chromatography using gradient of ethyl acetate in hexanes (0-40%) to yield 4-(tert-butyl)-N-(2-methoxypyridin-4-yl)-2-((6-(trifluoromethyl)pyridin-3-yl)oxy)benzamide (137 mg, 60%). ESI-MS m/z calc. 445.16. found 446.3 (M+1)+; Retention time: 1.87 minutes (3 minutes run).

Workup

  1. customThe reaction was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f2a2e0105d8d4a3baf99dce9f4f9bb20
Source dataset
uspto-grants-2016_07
Patent number
US09393235B2

Reaction notes

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