Pyrrolidine → HCID 131728125, compound

HRID 2237760Notes

Reaction equation

HRID 2237760 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:17][N:16]2[C:12](=[N:13][C:14]3[CH:21]=[C:20]([C:22]([OH:24])=O)[CH:19]=[CH:18][C:15]=32)[CH2:11][C@@H:10]1[C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=1[F:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=N1.N1CCCC1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:17][N:16]2[C:12](=[N:13][C:14]3[CH:21]=[C:20]([C:22]([N:37]4[CH2:38][CH2:43][CH2:42][CH2:41]4)=[O:24])[CH:19]=[CH:18][C:15]=32)[CH2:11][C@@H:10]1[C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=1[F:33])([CH3:2])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67421148HCID 67421148, compound

Product 1

HCID 131728125HCID 131728125, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 55 mg (0.12 mmol) of the product from Step C with 24 mg (0.18 mmol) of 1-hydroxybenzotriazole, 0.015 mL (0.18 mmol) of pyrrolidine, and 0.031 mL (0.18 mmol) of N,N-diisopropylethylamine in 1.0 mL of DMF was added 35 mg (0.18 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. The resulting mixture was stirred at ambient temperature for 16 h, then concentrated and purified directly by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 5% to 80% acetonitrile/water with 0.1% TFA) to give the title compound. LC/MS 515.2 (M+1).

Workup

  1. concentrationconcentrated
  2. custompurified directly by reverse phase HPLC (YMC Pro-C18 column, gradient elution, 5% to 80% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-7ecf3e53dde04fca95419f815de2f863
Source dataset
uspto-grants-2010_05
Patent number
US07718667B2

Reaction notes

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