Triethylamine → HCID 178425142, compound

HRID 2170489Notes

Reaction equation

HRID 2170489 reaction equation
[CH3:1][CH:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=O)=[CH:10][C:5]=2[O:4][CH2:3]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.[NH2:45][CH2:46][C:47]1[C:48]([OH:55])=[N:49][C:50]([CH3:54])=[CH:51][C:52]=1[CH3:53]>ClCCl>[OH:55][C:48]1[C:47]([CH2:46][NH:45][C:11]([C:9]2[CH:8]=[CH:7][C:6]3[CH:2]([CH3:1])[CH2:3][O:4][C:5]=3[CH:10]=2)=[O:13])=[C:52]([CH3:53])[CH:51]=[C:50]([CH3:54])[N:49]=1

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 895812133-Methyl-2,3-dihydro-1-benzofuran-6-carboxylic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425142HCID 178425142, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-methyl-2,3-dihydrobenzofuran-6-carboxylic acid (100 mg, 0.56 mmol) in dichloromethane (50 mL) was added 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (35 mg, 0.5 mmol), triethylamine (32 mg, 0.7 mmol), stirred for 30 minutes. Then 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (27 mg, 0.4 mmol) was added and the mixture was stirred at room temperature for 12 hours. The mixture was washed with water (50 mL), dried over sodium sulphate, concentrated. The residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give the product N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-3-methyl-2,3-dihydrobenzofuran-6-carboxamide (75 mg, 43%) as white solid. LRMS (M+H+) m/z: calcd 367.23. found 367. HPLC Purity (214 nm): 97%. 1H NMR (300 MHz, CDCl3) δ 7.32-7.27 (m, 2H), 7.12-7.11 (m, 1H), 6.10 (s, 1H), 4.72-4.66 (m, 1H), 4.46 (s, 2H), 4.11-4.05 (m, 1H), 3.56-3.53 (m, 1H), 2.35 (s, 3H), 2.24 (s, 3H), 1.31 (d, J=7.2 Hz, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (50 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-a5ffe1cc5cdf44d3a2f022cb25d0f066
Source dataset
uspto-grants-2015_06
Patent number
US09051269B2

Reaction notes

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