Benzylamine → HCID 57919796, compound

HRID 554972Notes

Reaction equation

HRID 554972 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]([C:16]3[S:17][C:18]([C:22](O)=[O:23])=[C:19]([CH3:21])[N:20]=3)[C:8]2=[O:25])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:60]([NH2:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>CN(C)C=O>[CH2:60]([NH:67][C:22]([C:18]1[S:17][C:16]([N:9]2[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=3)[C:8]2=[O:25])=[N:20][C:19]=1[CH3:21])=[O:23])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 5

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57919906HCID 57919906, compound

Product 1

HCID 57919796HCID 57919796, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-(4-fluorobenzyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-4-methylthiazole-5-carboxylic acid in N,N-dimethylformamide is added N,N-diisopropylethylamine, followed by the addition of 1-hydroxybenzotriazole monohydrate and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The resulting mixture is stirred for 10 minutes and followed by the addition of benzylamine at ambient temperature. After stirred at ambient temperature for an additional 17 h, the mixture is concentrated in vacuo. The residue is poured into a saturated aqueous solution of sodium bicarbonate and then extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over sodium sulfate, and filtered. The filtrate is concentrated and purified by column chromatography to afford the title compound.

Workup

  1. stirringAfter stirred at ambient temperature for an additional 17 h
  2. concentrationthe mixture is concentrated in vacuo
  3. additionThe residue is poured into a saturated aqueous solution of sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated aqueous sodium bicarbonate solution, water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-69a81ae2d9e54294b36f50fb4a1bdae0
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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