Triethylamine → HCID 178425192, compound

HRID 1501045Notes

Reaction equation

HRID 1501045 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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.[NH2:49][CH2:50][C:51]1[C:52]([OH:59])=[N:53][C:54]([CH3:58])=[CH:55][C:56]=1[CH3:57]>ClCCl.O>[OH:59][C:52]1[C:51]([CH2:50][NH:49][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([CH2:8][NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:17][CH:16]=2)=[C:56]([CH3:57])[CH:55]=[C:54]([CH3:58])[N:53]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 888115Benzoic acid, 4-[(phenylamino)methyl]-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178425242HCID 178425242, compound

Product 1

HCID 178425192HCID 178425192, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-((Phenylamino)methyl)benzoic acid (150 mg, 0.66 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (301 mg, 0.79 mmol) and triethylamine (2 mL) were dissolved in dichloromethane (20 mL). The mixture was stirred for 0.5 hour. And then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (100 mg, 0.66 mmol) was added to the mixture. The mixture was stirred at 25° C. for 12 hours. To the mixture, water (10 mL) was added and the 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=20:1) to give N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-((phenylamino)methyl)benzamide (100 mg, 42%). LRMS (M+H+) m/z: calcd 361.18. found 361. HPLC purity (214 nm): 99%. 1H NMR (300 MHz, CD3OD): δ 7.75 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 7.06-7.04 (m, 2H), 6.60-6.58 (m, 3H), 6.11 (s, 1H), 4.49 (s, 2H), 4.37 (s, 2H), 2.36 (s, 3H), 2.24 (s, 3H).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 hours
  2. extractionthe mixture was extracted with dichloromethane (10 mL×3)
  3. dry with materialThe combined organic phase was dried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-c937ca067be745edaa0aaa61698fbae1
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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