Triethylamine → HCID 178425156, compound

HRID 1501074Notes

Reaction equation

HRID 1501074 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][CH:4]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.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.[NH2:53][CH2:54][C:55]1[C:56]([OH:63])=[N:57][C:58]([CH3:62])=[CH:59][C:60]=1[CH3:61]>ClCCl.O>[OH:63][C:56]1[C:55]([CH2:54][NH:53][C:16](=[O:18])[C:15]2[CH:14]=[CH:13][C:12]([CH:4]([O:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:3][CH:2]([CH3:1])[CH3:21])=[CH:20][CH:19]=2)=[C:60]([CH3:61])[CH:59]=[C:58]([CH3:62])[N:57]=1

Participants

7

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 56998584HCID 56998584, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425156HCID 178425156, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-Methyl-1-phenoxybutyl)benzoic acid (20 mg, 0.07 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (59 mg, 0.15 mmol) and triethylamine (2 mL) was dissolved in dichloromethane (20 mL). The mixture was stirred for 0.5 hour. And then added 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added to the mixture and the resultant mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 mL) was added and the reaction mixture was extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and then filtered. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(3-methyl-1-phenoxybutyl)benzamide (Compound I-49) (15 mg, 52%). LRMS (M+H+) m/z: calcd 418.23. found 418. HPLC purity (214 nm): 95%. 1H NMR (300 MHz, CD3OD): δ 7.73 (d, J=8.4 Hz, 2H), 7.42 (d, J=8.1 Hz, 2H), 7.13 (t, J=7.5 Hz, 2H), 6.83-6.79 (m, 3H), 6.09 (s, 1H), 5.26-5.21 (m, 1H), 4.47 (s, 2H) 2.34 (s, 3H), 2.23 (s, 3H), 1.95-1.82 (m, 2H), 1.61-1.56 (m, 1H), 1.02-0.95 (m, 6H).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane (10 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-9f895e137f7c4366b0f6fa27329d39e2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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