Triethylamine → HCID 178425149, compound

HRID 1500957Notes

Reaction equation

HRID 1500957 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:2]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.[NH2:46][CH2:47][C:48]1[C:49]([OH:56])=[N:50][C:51]([CH3:55])=[CH:52][C:53]=1[CH3:54]>ClCCl>[OH:56][C:49]1[C:48]([CH2:47][NH:46][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([CH:3]3[CH2:4][CH2:5][O:1][CH2:2]3)=[CH:14][CH:13]=2)=[C:53]([CH3:54])[CH:52]=[C:51]([CH3:55])[N:50]=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 838300274-(tetrahydrofuran-3-yl)benzoic acidHCID 178425242HCID 178425242, compound

Product 1

HCID 178425149HCID 178425149, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(tetrahydrofuran-3-yl)benzoic acid (100 mg, 0.52 mmol) in dichloromethane (20 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). The mixture was stirred for 0.5 hour. 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), the organic layer was concentrated. The residue was purified by preparative-HPLC to give Compound I-83 as a white solid (35 mg, 21%). LRMS (M+H+) m/z: calcd 326.16. found 326. 1H NMR (300 MHz, CD3OD): δ 7.75 (d, J=6 Hz, 2H), 7.36 (d, J=6 Hz, 2H), 6.10 (s, 1H), 4.48 (s, 2H), 4.06 (m, 2H), 4.03 (m, 1H), 3.88 (m, 1H), 3.70 (m, 1H), 2.37 (s, 3H), 2.35 (s, 3H), 2.00 (m, 2H).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washThe mixture was washed with water (50 mL)
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-9fe8e4eb637048419f42eb6c7dd39274
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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