Triethylamine → HCID 22405496, compound

HRID 441198Notes

Reaction equation

HRID 441198 reaction equation
[NH2:1][C:2]1[C:3](=[O:22])[N:4]([CH2:8][C:9]([NH:11][CH:12]([CH:19]([CH3:21])[CH3:20])[C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:10])[CH:5]=[CH:6][CH:7]=1.[C:23]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl>[C:23]1([CH2:29][CH2:30][C:31]([NH:1][C:2]2[C:3](=[O:22])[N:4]([CH2:8][C:9]([NH:11][CH:12]([CH:19]([CH3:20])[CH3:21])[C:13](=[O:18])[C:14]([F:16])([F:17])[F:15])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[O:32])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 64801Benzenepropanoyl chlorideHCID 10426076HCID 10426076, compound

Product 1

HCID 22405496HCID 22405496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 2-(3-amino-2-oxo-1,2-dihydro-1-pyridyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (0.399) in dichloromethane at 0° C. was added 3-phenylpropionyl chloride (0.247 g) and triethylamine (0.247 g). The mixture was allowed to stir for 2 h, was diluted with dichloromethane (100 mL), washed (1N hydrochloric acid, saturated aqueous sodium bicarbonate, brine), dried, and evaporated to give a residue which was purified by chromatography, using methanol:dichloromethane as an eluent (gradient, 0.5:99.5, 2:98), to yield the title compound; mp 154°-155° C.; NMR: 0.80-0.98 (m,6), 2.21 (m,1), 4.09(m, NHCH hydrate), 4.52-4.82 (m, NHCH keto, CH2CO), 6.23 (m), 7.15-7.34 (m), 7.91 (d, J=10, NH hydrate), 8.24 (dd,1, J=7.5, 1.5), 8.93 (d, NH keto), 9.26 (s, NH hydrate), 9.29 (s, NH keto).

Workup

  1. washwashed (1N hydrochloric acid, saturated aqueous sodium bicarbonate, brine)
  2. customdried
  3. customevaporated
  4. customto give a residue which
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-4f6b16d621bb449d9b55b4570481a582
Source dataset
uspto-grants-1996_05
Patent number
US05521179

Reaction notes

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