Triethylamine → HCID 178425166, compound

HRID 1501211Notes

Reaction equation

HRID 1501211 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[NH2:51][CH2:52][C:53]1[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=1[CH3:59]>ClCCl>[F:1][C:2]1[CH:10]=[C:9]([CH:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:51][CH2:52][C:53]1[C:54]([OH:61])=[N:55][C:56]([CH3:60])=[CH:57][C:58]=1[CH3:59])=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89580924HCID 89580924, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425166HCID 178425166, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-fluoro-4-(1-phenoxyethyl)benzoic acid (150 mg, 0.514 mmol), 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (353 mg, 0.84 mmol) was dissolved in 20 mL dichloromethane, and then added triethylamine (2 mL). After the mixture was stirred at room temperature for 10 minute, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (0.514 mmol, 96 mg) was added. The mixture was stirred at room temperature for 12 hours then washed with water (10 mL), extracted with dichloromethane (20 mL). The organic layer were concentrated and s purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give 2-fluoro-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenoxyethyl)benzamide (70 mg, 47%). LCMS (M+H+) m/z: calcd 394.17. found 394. 1H NMR (300 MHz, CD3OD) δ 7.69 (t, J=6.1 Hz, 1H), 7.28-7.13 (m, 4H), 6.86-6.81 (m, 3H), 6.06 (s, 1H), 5.43-5.41 (m, 1H), 4.47 (s, 2H), 2.34 (s, 3H), 2.22 (s, 3H). 1.57 (d, J=6.6 Hz, 3H).

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. washthen washed with water (10 mL)
  3. extractionextracted with dichloromethane (20 mL)
  4. concentrationThe organic layer were concentrated
  5. customs purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-d7246cf1b2b34014bff8ec774d9160c8
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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