Triethylamine → HCID 54704657, compound

HRID 2214706Notes

Reaction equation

HRID 2214706 reaction equation
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4][NH2:5].[CH2:8](N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:19][N:20]([CH3:32])[C:21](=[O:31])[CH:22]=[C:23]1[C:27](=[O:28])OC(C)(C)[O:24]1>CO>[Cl:15][C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][C:35]=1[Cl:36])[CH2:19][N:20]([CH3:32])[C:21]([C:22]1[CH2:8][N:5]([CH2:4][C:3]([F:7])([F:6])[F:2])[C:27](=[O:28])[C:23]=1[OH:24])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 54704657HCID 54704657, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred warm (60° C.) solution of 2,2,2-trifluoroethylamine hydrochloride (100 mg, 1.0 mmol) paraformaldehyde (32 mg, 1.0 mmol) and triethylamine (0.14 mL, 1.0 mmol) in methanol (5 mL) was added N-(3,4-dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (344 mg, 1.0 mmol). After 24 h, the reaction mixture was cooled and purified by preparative HPLC using a C18 column and water/methanol-(0.1% TFA) as eluent. The fractions containing the desired product were combined, concentrated and lyophilized to give the title compound as a white powder (81.4 mg, 21% yield). 1HNMR (500 MHz, CDCl3) δ: 10.05 (1H, br s), 7.42 (1H, d, J=8.2 Hz), 7.36 (1H, s), 7.11 (1H, d, J=8.2 Hz), 4.60 (2H, s), 4.32 (2H, s), 4.10 (2H, q, 8.9 Hz), 3.04 (3H, s). HRMS calcd for C15H12Cl2F3N2O3 (M−H): 395.0177. found: 395.0192.

Workup

  1. temperaturethe reaction mixture was cooled
  2. custompurified by preparative HPLC
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0608da6e102d4fed8c74e8193da80b30
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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