Ethylamine hydrochloride → HCID 59749217, compound

HRID 896622Notes

Reaction equation

HRID 896622 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][CH2:14][CH2:15][N:16]1[C:20]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:19][S:18][C:17]1=[N:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[O:36][CH3:37])[CH2:9][C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:39]([NH2:41])[CH3:40].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C>O.CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH2:13][CH2:14][CH2:15][N:16]1[C:20]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:19][S:18][C:17]1=[N:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=1[O:36][CH3:37])[CH2:9][C:10]([NH:41][CH2:39][CH3:40])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22350974HCID 22350974, compound

Product 1

HCID 59749217HCID 59749217, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of the carboxylic acid compound (1.0 g) obtained in Example 327 (1), ethylamine hydrochloride (297 mg), 1-hydroxybenzotriazole monohydrate (418 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg) and N,N-dimethylformamide (7 ml) was added dropwise N,N-diisopropylethylamine (1.27 ml), and the mixture was stirred overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (1:1)] to give the title compound (929 mg) as foam. (2) N2-{3-[2-[(4-chloro-2-methoxyphenyl)imino]-4-(4-fluorophenyl)thiazol-3(2H)-yl]propyl}-N1-ethylglycinamide

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-983e83f53e704cee96d2c4ebf7944662
Source dataset
uspto-grants-2005_07
Patent number
US06919361B2

Reaction notes

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