1-Hydroxybenzotriazole → HCID 66854393, compound

HRID 1874001Notes

Reaction equation

HRID 1874001 reaction equation
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)([OH:3])[OH:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[F:44][C:45]1([F:50])[CH2:49][CH2:48][NH:47][CH2:46]1>C(#N)C>[F:44][C:45]1([F:50])[CH2:49][CH2:48][N:47]([C:8]([C:7]2[CH:6]=[CH:5][C:4]([B:1]([OH:2])[OH:3])=[CH:12][CH:11]=2)=[O:10])[CH2:46]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 3121834-Carboxyphenylboronic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27828273,3-Difluoropyrrolidine

Product 1

HCID 66854393HCID 66854393, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-boronobenzoic acid (500 mg, 3.01 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (866 mg, 4.52 mmol) and 1-hydroxybenzotriazole (554 mg, 3.62 mmol) in acetonitrile (25 mL) was sonicated until it became a solution. N,N-Diisopropylethylamine (1.579 mL, 9.04 mmol) and 3,3-difluoropyrrolidine (484 mg, 4.52 mmol) were added. After 30 min at room temperature, the mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (3×). The combined extracts were washed with brine, water, dried (Na2SO4) and concentrated. Reverse phase HPLC purification gave the expected product (0.250 mg, 33% yield). MS (ES+) m/z: 256 (M+H); LC retention time: 1.87 min (analytical HPLC Method A).

Workup

  1. customwas sonicated until it
  2. customthe mixture was quenched with saturated NH4Cl (50 mL)
  3. extractionextracted with EtOAc (3×)
  4. washThe combined extracts were washed with brine, water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-09df6f1dbf4e441ea32bedc890071c24
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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