Triethylamine → HCID 58188363, compound

HRID 1845255Notes

Reaction equation

HRID 1845255 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:6]([OH:8])=O.[CH3:19][C:20]1[N:25]=[CH:24][C:23]([C@H:26]([NH2:28])[CH3:27])=[CH:22][N:21]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:6]([NH:28][C@@H:26]([C:23]1[CH:22]=[N:21][C:20]([CH3:19])=[N:25][CH:24]=1)[CH3:27])=[O:8]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 58188145HCID 58188145, compound

Product 1

HCID 58188363HCID 58188363, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a round-bottom flask were charged 3-methoxy-5-(5-methylpyridin-2-yl)benzoic acid (26 mg, 0.11 mmol), (R)-1-(2-methylpyrimidin-5-yl)ethanamine (29 mg, 0.21 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (41 mg, 0.21 mmol), 1-hydroxybenzotriazole hydrate (33 mg, 0.21 mmol), triethylamine (22 mg, 0.21 mmol) and methylene chloride (3 mL). The mixture was stirred at room temperature overnight, and then concentrated. The residue was purified via preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH]) to afford the desired product as a white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via preparative HPLC (100×21.2 mm C18 column, CH3CN/water[10 mM Et2NH])

Sources & evidence

ORD record
ord-14971e6ca6064551a81d1f93c64a4aae
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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