Dimethylformamide → HCID 59749217, compound

HRID 747525Notes

Reaction equation

HRID 747525 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH:17][CH2:18][C:19](O)=[O:20])[C:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:11][S:10]2)=[C:4]([O:29][CH3:30])[CH:3]=1.[ClH:31].[CH2:32]([NH2:34])[CH3:33].[OH2:35].ON1C2C=C[CH:44]=[CH:45][C:40]=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH:58](N(CC)C(C)C)(C)C.CN(C)[CH:69]=[O:70]>O>[C:45]([O:35][C:69]([N:17]([CH2:16][CH2:15][CH2:14][N:13]1[C:12]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[CH:11][S:10][C:9]1=[N:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:31])=[CH:3][C:4]=1[O:29][CH3:30])[CH2:18][C:19]([NH:34][CH2:32][CH3:33])=[O:20])=[O:70])([CH3:44])([CH3:40])[CH3:58]

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22350943HCID 22350943, compound

Product 1

HCID 59749217HCID 59749217, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the carboxylic acid compound (1.0 g) obtained in Example 327 (1), ethylamine hydrochloride (297 mg), 1-hydroxybenzo-triazole 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.

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-b3d5bbff24df4caaa755f9e2a08c0963
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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