Cyclopropylamine → HCID 67118843, compound

HRID 1189024Notes

Reaction equation

HRID 1189024 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[C:18]([O:20][CH:21]([CH3:23])[CH3:22])[CH:19]=2)[NH:16][C:15]([C:24]2[S:25][CH:26]([CH2:29][C:30]([OH:32])=O)[CH2:27][N:28]=2)=[CH:14]3)=[CH:6][CH:5]=1.Cl.C(N=C=N[CH2:39][CH2:40][CH2:41][N:42](C)C)C.ON1C2C=CC=CC=2N=N1.C1(N)CC1>O.CN(C)C=O>[CH:41]1([NH:42][C:30](=[O:32])[CH2:29][CH:26]2[S:25][C:24]([C:15]3[NH:16][C:17]4[C:13]([CH:14]=3)=[CH:12][C:11]([O:10][C:7]3[CH:8]=[N:9][C:4]([CH2:3][O:2][CH3:1])=[CH:5][CH:6]=3)=[CH:19][C:18]=4[O:20][CH:21]([CH3:23])[CH3:22])=[N:28][CH2:27]2)[CH2:39][CH2:40]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67118526HCID 67118526, compound

Product 1

HCID 67118843HCID 67118843, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of {2-[5-{[6-(methoxymethyl)pyridin-3-yl]oxy}-7-(1-methylethoxy)-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetic acid (300 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (190 mg), 1-hydroxybenzotriazole (130 mg), cyclopropylamine (75 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 15 h. Water was added to the mixture and the resultant was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio) to give yellow crystals. The crystals were recrystallized from ethyl acetate-hexane to give the title compound (170 mg, 52%) as pale yellow prisms. MS 495 (MH+). mp 100-101° C.

Workup

  1. extractionthe resultant was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 95:5, volume ratio)
  7. customto give yellow crystals
  8. customThe crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-922c1fad76c341c789d559dea5e40d6c
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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