1-Hydroxybenzotriazole → HCID 57720185, compound

HRID 1985853Notes

Reaction equation

HRID 1985853 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:11][NH:12][C:13]1[N:17]([C@@H:18]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[N:14]=1)(O)=[O:2].Cl.[NH2:41][CH2:42][C:43]([NH2:45])=[O:44].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[C:43]([CH2:42][NH:41][C:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:11][NH:12][C:13]1[N:17]([C@@H:18]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[C:16]2[CH:27]=[CH:28][CH:29]=[CH:30][C:15]=2[N:14]=1)=[O:2])(=[O:44])[NH2:45]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2723639Glycinamide hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57720249HCID 57720249, compound

Product 1

HCID 57720185HCID 57720185, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

2-[3-(3-Carboxypropoxy)-4-phenylbenzylamino]-1-(β-D-ribofuranosyl)-1H-benzimidazole (50 mg), glycinamide hydrochloride (17 mg), 1-hydroxybenzotriazole (29 mg) and triethylamine (47 mg) were suspended in N,N-dimethylformamide (2 mL) at room temperature. To the mixture was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (36 mg), and the mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated 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 (23 mg).

Workup

  1. concentrationThe reaction mixture was concentrated 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-d50ec2b53e9644b59b3845360d49bd85
Source dataset
uspto-grants-2009_06
Patent number
US07547680B2

Reaction notes

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