Ammonia → HCID 57476406, compound

HRID 1994996Notes

Reaction equation

HRID 1994996 reaction equation
[F:1][C:2]1[C:10]2[C:5](=[C:6]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:14])=[O:13])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:21]1[S:22][CH:23]([CH2:26][C:27]([OH:29])=O)[CH2:24][N:25]=1.Cl.C([N:33]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.N>O1CCCC1.C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[C:10]2[C:5](=[C:6]([N:11]([CH3:20])[S:12]([C:15]3[S:16][CH:17]=[CH:18][CH:19]=3)(=[O:13])=[O:14])[CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:21]1[S:22][CH:23]([CH2:26][C:27]([NH2:33])=[O:29])[CH2:24][N:25]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59135752(2-{3-fluoro-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid

Product 1

HCID 57476406HCID 57476406, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-{3-fluoro-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (97.2 mg) in tetrahydrofuran (2 mL) and acetonitrile (2 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (48 mg) and 1-hydroxybenzotriazole monohydrate (39 mg), and the mixture was stirred at room temperature for 1 hr. Aqueous ammonia (28%, 2 mL) was added, and the mixture was stirred at room temperature for 30 min, and diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine, dried over anhydrous magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluate: ethyl acetate), and the obtained solid was recrystallized (ethyl acetate-diisopropyl ether) to give the title compound (50.1 mg, yield 53%) as a colorless solid. melting point 204-205° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe obtained solid was recrystallized (ethyl acetate-diisopropyl ether)

Sources & evidence

ORD record
ord-f520187b012a48d9a42de3ba8ef03170
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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