Serinol → HCID 68874607, compound

HRID 1985844Notes

Reaction equation

HRID 1985844 reaction equation
[C:1]([CH:4]=[CH:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][NH:10][C:11]1[N:15]([C@@H:16]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]2[OH:18])[C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=2[N:12]=1)([OH:3])=O.[NH2:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>O1CCCC1.C(N(CC)CC)C>[OH:35][CH2:34][CH:33]([NH:32][C:1]([CH:4]=[CH:5][C:6]1[CH:7]=[C:8]([CH:29]=[CH:30][CH:31]=1)[CH2:9][NH:10][C:11]1[N:15]([C@@H:16]2[O:22][C@H:21]([CH2:23][OH:24])[C@@H:19]([OH:20])[C@H:17]2[OH:18])[C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]=2[N:12]=1)=[O:3])[CH2:36][OH:37]

Participants

7

Reactant 4

HCID 68294SerinolHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68845447HCID 68845447, compound

Product 1

HCID 68874607HCID 68874607, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2-[3-(2-Carboxyvinyl)benzylamino]-1-(β-D-ribofuranosyl)-1H-benzimidazole (50 mg), 2-amino-1,3-propanediol (21 mg), 1-hydroxybenzotriazole (36 mg) and triethylamine (41 μL) were suspended in tetrahydrofuran (2 mL). To the mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (45 mg), and the mixture was stirred for 17 hours. The solvent was removed under reduced pressure, and the obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90) to give the title compound (52 mg)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe obtained residue was purified by preparative reverse phase column chromatography (Shiseido CAPSELL PAC C18UG80, 5 μm, 20×50 mm, flow rate 30 mL/minutes linear gradient, water/methanol=70/30-10/90)

Sources & evidence

ORD record
ord-b60dd1ae78154eb18cfae9f1d9401c14
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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