1-Hydroxybenzotriazole → HCID 178495997, compound

HRID 1863946Notes

Reaction equation

HRID 1863946 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:7]=[C:6]([C:8]([OH:10])=O)[NH:5][N:4]=1.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>ClCCl>[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH:17][C:8]([C:6]1[NH:5][N:4]=[C:3]([C:2]([F:1])([F:12])[F:11])[CH:7]=1)=[O:10]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524407HCID 178524407, compound

Product 1

HCID 178495997HCID 178495997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg (2.78 mmol) of 3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid, 0.333 mL (3.05 mmol) of aminoacetaldehyde dimethyl acetal, 588 mg (3.05 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), 510 mg (3.33 mmol) of 1-hydroxybenzotriazole (HOBT), 1.92 mL (11.1 mmol) of N,N-diisopropylethylamine, and 20 mL of dichloromethane was stirred at room temperature for 20 h and then concentrated. Purification of the residue by flash chromatography on silica gel (0-10% methanol in dichloromethane) afforded the title compound as a white solid. LC-MS 268 (M+1).

Workup

  1. concentrationconcentrated
  2. customPurification of the residue by flash chromatography on silica gel (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a95c34ef0c3c49249ab60f56c2524bc7
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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