Triethylamine → HCID 178425188, compound

HRID 1501019Notes

Reaction equation

HRID 1501019 reaction equation
[O:1]([C@H:8]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.[NH2:48][CH2:49][C:50]1[C:51]([OH:58])=[N:52][C:53]([CH3:57])=[CH:54][C:55]=1[CH3:56]>ClCCl.O>[OH:58][C:51]1[C:50]([CH2:49][NH:48][C:14](=[O:16])[C:13]2[CH:12]=[CH:11][C:10]([C@@H:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:9])=[CH:18][CH:17]=2)=[C:55]([CH3:56])[CH:54]=[C:53]([CH3:57])[N:52]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89581520HCID 89581520, compoundHCID 178425242HCID 178425242, compound

Product 1

HCID 178425188HCID 178425188, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-4-(1-phenoxyethyl)benzoic acid (121 mg, 0.5 mmol) in dichloromethane (20 mL) was added 1H-benzo[d][1,2,3]triazol-1-ol (135 mg, 1 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (190 mg, 1 mmol) and triethylamine (252 mg, 2.5 mmol), and stirred at room temperature for 0.5 hour, 3-(aminomethyl)-4,6-dimethylpyridin-2-ol (152 mg, 1 mmol) was added and stirred for 4 hours. To the reaction mixture was added water (20 mL), extracted with dichloromethane (20 mL) two times, combined and concentrated the organic layers, the residue was purified by chromatography with dichloromethane/methanol=20:1 to afford (S)—N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)-4-(1-phenoxyethyl)benzamide (Compound I-31) (150 mg, 80%). LRMS (M+H+) m/z: calcd for 376.18. found 376. HPLC Purity (214 nm): 96%. 1H NMR (300 MHz, DMSO-d6): δ 11.45 (s, 1H), 8.30 (t, J=5.1 Hz, 1H), 7.79 (d, J=8.1 Hz, 2H), 7.44 (d, J=8.1 Hz, 2H), 7.18 (t, J=7.2 Hz, 2H), 6.88-6.81 (m, 3H), 5.84 (s, 1H), 5.52 (q, J=6.3 Hz, 1H), 4.27 (d, J=4.8 Hz, 2H), 2.15 (s, 3H), 2.10 (s, 3H), 1.54 (d, J=6.6 Hz, 3H).

Workup

  1. stirringstirred for 4 hours
  2. extractionextracted with dichloromethane (20 mL) two times
  3. concentrationconcentrated the organic layers
  4. customthe residue was purified by chromatography with dichloromethane/methanol=20:1

Sources & evidence

ORD record
ord-462cb5a2a32e47cda6ffe682545f21c2
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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