Hydrochloric Acid → N-(4-aminobutyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetamide hydrochloride

HRID 16658

Reaction equation

HRID 16658 reaction equation
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=O.C(N[CH:34]([NH2:38])[CH2:35][CH2:36][CH3:37])(OC(C)(C)C)=O.Cl.C([N:42]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN(C1C=CC=CN=1)C.CCN(C(C)C)C(C)C.Cl>ClCCl.CN(C)C=O>[ClH:19].[NH2:42][CH2:37][CH2:36][CH2:35][CH2:34][NH:38][C:23](=[O:25])[CH2:22][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:20][CH3:21])[CH:5]=2)[N:10]([C:11](=[O:12])[C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:2]=1[CH3:1]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 3715IndomethacinHCID 218852-DimethylaminopyridineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22649557N-BOC butanediamine

Product 1

HCID 66813107N-(4-aminobutyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetamide hydrochlorideYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

a Fluorescent Indo-Dansyl Analog: Compound 27z was synthesized by the method outlined in FIG. 4. Briefly, indomethacin was complexed with N-BOC butanediamine for 16 hours at room temperature in the presence of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDCl), 1-hydroxybenzotriazole (HOBt), dimethylaminopyridine (DMAP), N,N′-diisopropylethylamine (DIPEA), and N,N-dimethylformamide (DMF). A yellow solid corresponding to a percent yield of 72% was obtained. This solid was then dissolved in dichloromethane and treated with HCl (gas) for 2 hours at room temperature, producing N-(4-aminobutyl)-2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetamide hydrochloride as a brown solid (98% yield), which was reacted with triethylamine (TEA) in dichloromethane for 5 minutes at room temperature prior to the addition of dansyl chloride. Dansyl chloride was then added, and the reaction was allowed to continue for 16 hours at room temperature, which produced Compound 27z as a yellow solid in a yield of 77%. Compound 27z was characterized by NMR and mass spectroscopy (MS).

Workup

  1. customA yellow solid corresponding to a percent yield of 72% was obtained

Sources & evidence

ORD record
ord-f3981a7fb92f45458d1435a91806c2dc
Source dataset
uspto-grants-2010_06
Patent number
US07736624B2

Linked notes

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