1-Hydroxybenzotriazole → HCID 67119182, compound

HRID 1189041Notes

Reaction equation

HRID 1189041 reaction equation
Cl.CN.[F:4][C:5]1[C:13]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:12]2[C:8]([CH:9]=[C:10]([C:19]3[S:20][CH:21]([CH2:24][C:25]([OH:27])=O)[CH2:22][N:23]=3)[NH:11]2)=[CH:7][C:6]=1[O:28][C:29]1[CH:30]=[N:31][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:34]=1.O[N:40]1[C:44]2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(N(CC)CC)C>[F:4][C:5]1[C:13]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:12]2[C:8]([CH:9]=[C:10]([C:19]3[S:20][CH:21]([CH2:24][C:25]([NH:40][CH3:44])=[O:27])[CH2:22][N:23]=3)[NH:11]2)=[CH:7][C:6]=1[O:28][C:29]1[CH:30]=[N:31][C:32]([S:35]([CH3:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6364545Methylamine hydrochlorideHCID 67118649HCID 67118649, compound

Product 1

HCID 67119182HCID 67119182, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To an ice-cooled and stirred mixture of methylamine hydrochloride (35 mg) and triethylamine (0.072 mL) in N,N-dimethylformamide (7 mL) were added {2-[6-fluoro-7-(2-methoxyethoxy)-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (135 mg), 1-hydroxybenzotriazole (70 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (100 mg). After stirring at 4° C. to room temperature for 15 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed successively with aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated to give colorless crystals, which were recrystallized from tetrahydrofuran-ethyl acetate to give the title compound (109 mg, 79%) as colorless crystals. MS 537 (MH+). mp 151-152° C.

Workup

  1. stirringAfter stirring at 4° C. to room temperature for 15 h
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe organic layer was washed successively with aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give colorless crystals, which
  8. customwere recrystallized from tetrahydrofuran-ethyl acetate

Sources & evidence

ORD record
ord-65c561e916bf4bb3be97472d5ad5d73e
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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