1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 58237047, compound

HRID 1189014Notes

Reaction equation

HRID 1189014 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]([CH2:20][C:21](O)=[O:22])[CH2:18][N:19]=1)=[CH:11]2.Cl.C([N:39]=C=NCCCN(C)C)C.[NH4+].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:1][O:2][CH2:3][CH:4]([CH3:35])[O:5][C:6]1[CH:7]=[C:8]([O:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:27][CH:26]=2)[CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]([CH2:20][C:21]([NH2:39])=[O:22])[CH2:18][N:19]=1)=[CH:11]2

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 58237049HCID 58237049, compound

Product 1

HCID 58237047HCID 58237047, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-{7-(2-methoxy-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (48 mg) in N,N-dimethylformamide (2 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (35 mg) and 1-hydroxybenzotriazole ammonium salt (28 mg) at room temperature. The mixture was stirred at room temperature over night. The mixture was concentrated in vacuo. Ethyl acetate was added to the residue and the resultant was washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio) to give the title compound. The compound was triturated and washed with diethyl ether-ethyl acetate-hexane to give the title compound (11 mg, 23%) as a white powder. mp 107-112° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionEthyl acetate was added to the residue
  3. washthe resultant was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=100:0 to 90:10, volume ratio)

Sources & evidence

ORD record
ord-8255c49e1443437e8a916cd12a41a6b0
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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